Organic compound and organic electroluminescent device comprising the same

ABSTRACT

The present disclosure relates to a novel organic compound and an organic electroluminescent device comprising the same, and the organic compound of the present disclosure may be used for an organic material layer of the organic electroluminescent device, thereby improving the light emitting efficiency, driving voltage, lifetime, and the like of the organic electroluminescent device.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a National Stage of International Application No.PCT/KR2015/0034734, filed on Apr. 7, 2015, which claims priority fromKorean Patent Application No. 10-2014-0042512, filed on Apr. 9, 2014,the contents of all of which are incorporated herein by reference intheir entirety.

TECHNICAL FIELD

The present disclosure relates to a novel organic compound and anorganic electroluminescent device comprising the same.

BACKGROUND ART

Since 1965, studies on an organic electroluminescent (EL) device(hereinafter, simply referred to as an ‘organic EL device’) leading toblue electric light emission using an anthracene single crystal had beencontinuously conducted, and in 1987, an organic EL device having atwo-layer laminated structure including a hole layer (NPB) and a lightemitting layer (Alq₃) was proposed by Tang. Since then, the organic ELdevice has been proposed in the form of a multilayer-laminated structurewhich imparts each characteristic and subdivided function, such as anorganic layer which is responsible for injecting and transporting holes,an organic layer which is responsible for injecting and transportingelectrons, and an organic layer which induces electroluminescence tooccur due to the combination of holes and electrons in the device inorder to implement high efficiency and long lifetime characteristicsrequired for commercialization.

In the organic EL device, when voltage is applied between twoelectrodes, holes are injected into the organic material layer at theanode, and electrons are injected into the organic material layer at thecathode. When the injected holes and electrons meet each other, anexciton is formed, and when the exciton falls down to a bottom state,light is emitted. Materials included in the organic material layer maybe classified into a light emitting material, a hole injection material,a hole transporting material, an electron transporting material, anelectron injection material, and the like according to the function.

In the electron spins of the excitons formed by recombining electronsand holes, the singlet exciton and the triplet exciton are produced at aratio of 25% and 75%, respectively. In this case, the organic EL devicemay be classified into a fluorescent EL device in which singlet excitonscontribute to light emission and a phosphorescent EL device in whichtriplet excitons contribute to light emission, according to the type ofelectron spin of the excitons formed.

In the fluorescent EL device in which light is emitted by singletexcitons, it is impossible for the internal quantum efficiency totheoretically exceed 25% according to the production ratio, and theexternal quantum efficiency of 5% is accepted as the limitation.

In the phosphorescent EL device in which light is emitted by tripletexcitons, when a metal complex compound including a transition metalheavy atom such as Jr and Pt is used as a phosphorescent dopant, thelight emitting efficiency may be improved up to 4 times compared to thefluorescent electroluminescent device.

As described above, the phosphorescent EL device exhibits theoreticallyhigher efficiency than that of the fluorescent EL device in terms oflight emitting efficiency. However, unlike green or red phosphorescentdevices, in blue phosphorescent devices, the level of development forthe color purity of a dark blue color, a phosphorescent dopant with highefficiency, and a host with a wide energy gap has been so little thatcommercialization has not even started, and instead, a blue fluorescentdevice has been used in products.

As the performance of the organic EL device has been improved to thelevel of commercialization characteristics due to the introduction of amultilayer-laminated structure, it has been attempted to expand theapplication range of the organic EL device from the start of a radiodisplay product for a vehicle since 1997 to a mobile information displaydevice and a display device for TV.

Further, according to the recent trends of an increase in size and ahigh resolution in a display, there is a need for developing an organicEL display having high efficiency and a long lifetime. In particular,the high resolution in a display may be implemented when more pixels areformed in the same area. Due to the high resolution, the light emittingarea of the organic EL pixels has decreased, thereby resulting inreduction in the lifetime of the device. This reduction in the lifetimeof the device has become the most important technical problem that theorganic EL device needs to overcome.

However, since the materials for the organic EL device in the relatedart have a low glass transition temperature and thus are very poor inthermal stability, the materials fail to reach a level which issatisfactory in terms of a lifetime of an organic EL device, and need tobe improved even in terms of light emitting characteristics.

DISCLOSURE Technical Problem

Therefore, an object of the present disclosure is to provide a novelcompound which has excellent carrier transporting capability and lightemitting capability, and the like, and thus may be used as a material oflight emitting layer, a material of hole transport layer, a material oflight emitting auxiliary layer, a material of electron transportauxiliary layer, and the like.

Further, another object of the present disclosure is to provide anorganic electroluminescent device which includes the novel compound tohave a low driving voltage, high light emitting efficiency, and animproved lifetime.

Technical Solution

The present disclosure provides a compound represented by the followingFormula 1:

in Formula 1,

one of R₁ and R₂, R₂ and R₃, R₃ and R₄, R₄ and R₅, R₅ and R₆, R₆ and R₇,and R₇ and R₈ combines with each other to form a fused ring representedby the following Formula 2;

in Formula 2,

a dotted line is a portion to be bonded to Formula 1,

X₁ is selected from the group consisting of N(Ar₁), O, S, C(Ar₂)(Ar₃),and Si(Ar₄)(Ar₅),

Y₁ to Y₄ are each independently N or C(R₉),

Ar₁ to Ar₅ are the same as or different from each other, and are eachindependently selected from the group consisting of a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms,a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms,a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀alkylsilyl group, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, ormay combine with an adjacent group to form a fused ring,

R₁ to R₈, which do not form the fused ring of Formula 2, and R₉ are thesame as or different from each other, and are each independentlyselected from the group consisting of hydrogen, deuterium (D), halogen,a cyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀ cycloalkyl group,a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀ arylgroup, a heteroaryl group having 5 to 60 nuclear atoms, a C₁ to C₄₀alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkylsilyl group,a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, or maycombine with an adjacent group to form a fused ring, and

the alkyl group, the alkenyl group, the alkynyl group, the cycloalkylgroup, the heterocycloalkyl group, the aryl group, the heteroaryl group,the alkyloxy group, the aryloxy group, the alkylsilyl group, thearylsilyl group, the alkylboron group, the arylboron group, thearylphosphine group, the arylphosphine oxide group, and the arylaminegroup of Ar₁ to Ar₅ and R₁ to R₉ are each independently unsubstituted orsubstituted with one or more substituents selected from the groupconsisting of deuterium, halogen, a cyano group, a nitro group, a C₁ toC₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, aC₃ to C₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40nuclear atoms, a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60nuclear atoms, a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, aC₁ to C₄₀ alkylsilyl group, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀alkylboron group, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphinegroup, a C₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylaminegroup, and in this case, the substituent may combine with an adjacentgroup to form a fused ring, and when the substituent is present inplural numbers, the substituents are the same as or different from eachother.

Further, the present disclosure provides an organic electroluminescentdevice including an anode, a cathode, and one or more organic materiallayers interposed between the anode and the cathode, in which at leastone of the organic material layers comprises the above-describedcompound represented by Formula 1.

Advantageous Effects

The compound of the present disclosure has excellent thermal stability,carrier transporting capability, light emitting capability, and thelike, and thus may be usefully applied as a material of organic materiallayer for an organic electroluminescent device.

Further, for the organic electroluminescent device including thecompound of the present disclosure in an organic material layer, theaspects such as light emitting performance, driving voltage, lifetime,and efficiency may be significantly improved, and accordingly, theorganic electroluminescent device may be effectively applied to afull-color display panel, and the like.

BEST MODE

Hereinafter, the present disclosure will be described.

In the organic compound according to the present disclosure, an indolemoiety, a benzothiophene moiety, a benzofuran moiety, or the like isfused with dibenzo[b,e][1,4]dioxine to form a basic skeleton, and theorganic compound has a structure in which various substituents arebonded to or fused with the basic skeleton, and is represented byFormula 1.

In general, the phosphorescent light emitting layer in the organicmaterial layers included in the organic electroluminescent deviceincludes a host and a dopant in order to increase the color purity andthe light emitting efficiency. In this case, the host needs to have ahigher triplet energy gap than that of the dopant. That is, in order toeffectively provide a phosphorescent light emission from the dopant, thelowest excitation state energy of the host needs to be higher than thelowest emission state energy of the dopant. The compound represented byFormula 1 has a wide singlet energy level and a high triplet energylevel in which the dibenzo[b,e][1,4] dioxine portion. A specificsubstituent may be introduced into the indole moiety which is fused withdibenzo[b,e][1,4]dioxine to exhibit a higher energy level than that ofthe dopant when the compound of Formula 1 is applied as a host of thelight emitting layer.

Further, since the compound represented by Formula 1 has a high tripletenergy as described above, it is possible to prevent diffusing (moving)an exciton produced from a light emitting layer to an adjacent electrontransport layer or an adjacent hole transport layer. Accordingly, whenthe compound of Formula 1 is used to form an organic material layer(hereinafter, referred to as a ‘light emitting auxiliary layer’) betweena hole transport layer and a light emitting layer or form an organicmaterial layer (hereinafter, referred to as an ‘electron transportauxiliary layer’) between a light emitting layer and an electrontransport layer, the diffusion of excitons is prevented by the compound,so that the number of excitons substantially contributing to lightemission in the light emitting layer is increased, and thus the lightemitting efficiency of the device may be improved, unlike an organicelectroluminescent device in the related art, which does not include thelight emitting auxiliary layer or the electron transport auxiliarylayer.

Further, the compound represented by Formula 1 may have a wide bandgapand high carrier transporting property because the HOMO and LUMO energylevels may be adjusted according to the substituent to be introducedinto the basic skeleton.

Additionally, the compound of the present disclosure may be easily usedas a material of hole transport layer when an electron donating group(EDG) having a high electron donating property is bonded to the basicskeleton due to high hole transporting capability of an oxygen atom inthe dibenzo[b,e][1,4]dioxine. Further, when an electron withdrawinggroup (EWG) having a high electron absorbing property is bonded to thebasic skeleton, the entire molecule has bipolar characteristics, andthus may increase the binding power of holes and electrons.

Furthermore, according to the compound represented by Formula 1 of thepresent disclosure, the molecular weight of the compound issignificantly increased as various substitution products, particularly,an aryl group and/or a heteroaryl group, are introduced into the basicskeleton, and accordingly, the glass transition temperature is enhanced,so that the compound represented by Formula 1 of the present disclosuremay have thermal stability higher than that of the organic materiallayer material in the related art (for example, CBP). Further, thecompound represented by Formula 1 is also effective for suppressingcrystallization of the organic material layer.

As described above, when the compound represented by Formula 1 of thepresent disclosure is applied as a material of organic material layermaterial for an organic electroluminescent device, preferably a materialof light emitting layer (a blue, green, and/or red phosphorescent hostmaterial), a material of electron transport layer/injection layer, amaterial of hole transport layer/injection layer, a material of lightemitting auxiliary layer, and a material of lifetime improvement layer,the performance and lifetime characteristics of the organicelectroluminescent device may be greatly enhanced. The organicelectroluminescent device may resultantly maximize the performance of afull-color organic light emitting panel.

When one of R₁ and R₂, R₂ and R₃, R₃ and R₄, R₄ and R₅, R₅ and R₆, R₆and R₇, and R₇ and R₈ combines with each other to form a fused ringrepresented by the following Formula 2, the compound of Formula 1 may berepresented by any one selected from the following Formulae 3 to 5.

In Formulae 3 to 5,

X₁, Y₁ to Y₄, and R₁ to R₈ are each the same as those defined in Formula1.

The R₁ to R₈, which do not form the fused ring of Formula 2, are thesame as or different from each other, and are each independentlyselected from a group consisting of hydrogen, deuterium (D), halogen, acyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀ arylgroup, a heteroaryl group having 5 to 60 nuclear atoms, a C₁ to C₄₀alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkylsilyl group,a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, or maycombine with an adjacent group to form a fused ring.

In Formula 2, a dotted line means a portion bonded to Formula 1.

The X₁ is selected from a group consisting of N(Ar₁), O, S, C(Ar₂)(Ar₃),and Si(Ar₄)(Ar₅), and may be preferably selected from a group consistingof N(Ar₁), O, and S.

The Ar₁ to Ar₅ are the same as or different from each other, and areeach independently selected from a group consisting of a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms,a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms,a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀alkylsilyl group, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, ormay combine with an adjacent group to form a fused ring.

Preferably, the Ar₁ to Ar₅ are the same as or different from each other,and may be each independently selected from a group consisting of a C₆to C₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

The Y₁ to Y₄ are each independently N or C(R₉), and may be allpreferably C(R₉). In this case, when C(R₉) is present in plural numbers,a plurality of C(R₉)'s is the same as or different from each other.

The R₉ is selected from a group consisting of hydrogen, deuterium (D),halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ toC₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀ cycloalkylgroup, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ toC₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C₁ toC₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkylsilylgroup, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, or maycombine with an adjacent group to form a fused ring.

Preferably, the R₉ may be selected from a group consisting of hydrogen,deuterium (D), a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60nuclear atoms, and a C₆ to C₆₀ arylamine group.

The alkyl group, the alkenyl group, the alkynyl group, the cycloalkylgroup, the heterocycloalkyl group, the aryl group, the heteroaryl group,the alkyloxy group, the aryloxy group, the alkylsilyl group, thearylsilyl group, the alkylboron group, the arylboron group, thearylphosphine group, the arylphosphine oxide group, and the arylaminegroup of Ar₁ to Ar₅, R₁ to R₈, which do not form the fused ring ofFormula 2, and R₉ are each independently unsubstituted or substitutedwith one or more substituents selected from a group consisting ofdeuterium, halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms,a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms,a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀alkylsilyl group, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylamine group,and the substituent may combine with an adjacent group to form a fusedring. In this case, when the substituent is present in plural numbers, aplurality of substituents is the same as or different from each other.

Alternatively, at least one of the Ar₁ to Ar₅, R₁ to R₈, which do notform the fused ring of Formula 2, and R₉ preferably at least one of theAr₁ to Ar₅ and R₉ may be a substitution product represented by thefollowing Formula 6.

In Formula 6,

L₁ is a single bond (direct bond), or selected from a group consistingof a C₆ to C₁₈ arylene group and a heteroarylene group having 5 to 18nuclear atoms, or may combine with an adjacent substituent (for example,R_(a), R_(b)) to form a fused ring,

R_(a) and R_(b) are the same as or different from each other, and areeach independently a substitution product selected from a groupconsisting of a C₁ to C₄₀ alkyl group, a C₆ to C₆₀ aryl group, and aheteroaryl group having 5 to 60 nuclear atoms, or represented by thefollowing Formula 7 or 8, or may combine with an adjacent substituent(for example, L₁) to form a fused ring,

in Formulae 7 and 8,

X and Y are each a 6-membered aromatic ring,

L₁₁ and L₁₂ are each a single bond, or selected from a group consistingof a C₆ to C₁₈ arylene group and a heteroarylene group having 5 to 18nuclear atoms,

Ar₆ is selected from a group consisting of a C₆ to C₁₈ aryl group and aheteroaryl group having 5 to 18 nuclear atoms,

a, b, and d are each an integer of 0 to 4, and the case where the a, b,and d are 0 means that hydrogen is not substituted with the substituentR_(c), R_(d), or R_(f), and when the a, b, and d are each an integer of1 to 3, R_(c), R_(d), and R_(f) are each selected from a groupconsisting of deuterium, halogen, a cyano group, a nitro group, a C₁ toC₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, aC₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, aC₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₃ to C₄₀cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms,a C₆ to C₆₀ arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀alkylboron group, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphinegroup, a C₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilylgroup,

c is an integer of 0 to 3, and the case where the c is 0 means thathydrogen is not substituted with the substituent R_(c), and when the cis 1 to 3, R_(c) is selected from a group consisting of deuterium,halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ toC₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, aheteroaryl group having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxygroup, a C₁ to C₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group,

in this case, a plurality of R_(c)'s is the same as or different fromeach other, a plurality of R_(d)'s is the same as or different from eachother, a plurality of R_(e)'s is the same as or different from eachother, and a plurality of R_(f)'s is the same as or different from eachother, and

the arylene group and the heteroarylene group of L₁ and the alkyl group,the aryl group, and the heteroaryl group of R_(a) and R_(b) are eachindependently unsubstituted or substituted with one or more substituentsselected from a group consisting of deuterium, halogen, a cyano group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ toC₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroaryl group having 5to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxygroup, a C₆ to C₆₀ arylamine group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₁ to C₄₀alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylborongroup, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxidegroup, and a C₆ to C₆₀ arylsilyl group.

Further, at least one of the Ar₁ to Ar₅, R₁ to R₈, which do not form thefused ring of Formula 2, and R₉ preferably at least one of the Ar₁ toAr₅ and R₉ may be a substitution product represented by the followingFormula 9.

In Formula 9,

L₂ is a single bond (direct bond) or selected from a group consisting ofa C₆ to C₁₈ arylene group and a heteroarylene group having 5 to 18nuclear atoms,

Z₁ to Z₅ are the same as or different from each other, and are eachindependently N or C(R₁₁),

in this case, at least one of Z₁ to Z₅ is N,

when C(R₁₁) is present in plural numbers, a plurality of C(R₁₁)'s is thesame as or different from each other,

R₁₁ is selected from a group consisting of hydrogen, deuterium, halogen,a cyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀alkenyl group, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, aheteroaryl group having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxygroup, a C₁ to C₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, ormay combine with an adjacent group to form a fused ring, and

the arylene group and the heteroarylene group of L₂ and the alkyl group,the alkenyl group, the alkynyl group, the aryl group, the heteroarylgroup, the aryloxy group, the alkyloxy group, the cycloalkyl group, theheterocycloalkyl group, the arylamine group, the alkylsilyl group, thealkylboron group, the arylboron group, the arylphosphine group, thearylphosphine oxide group, and the arylsilyl group of R₁₁ are eachindependently unsubstituted or substituted with one or more substituentsselected from a group consisting of deuterium, halogen, a cyano group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ toC₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroaryl group having 5to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxygroup, a C₆ to C₆₀ arylamine group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₁ to C₄₀alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylborongroup, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxidegroup, and a C₆ to C₆₀ arylsilyl group.

Further, at least one of the Ar₁ to Ar₅, R₁ to R₈, which do not form thefused ring of Formula 2, and R₉ preferably at least one of the Ar₁ toAr₅ and R₉ may be selected from a group consisting of substituentsrepresented by the following Formulae A-1 to A-15.

In Formulae A-1 to A-15,

L₂ and L₁₁ are each the same as those defined in Formula 9,

n is an integer of 0 to 4, and the case where the n is 0 means thathydrogen is not substituted with the substituent R₂₁, and when the n isan integer of 1 to 4, R₂₁ is selected from a group consisting ofdeuterium, halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C₆ to C₆₀aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group,a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, ormay combine with an adjacent group to form a fused ring, and

the alkyl group, the alkenyl group, the alkynyl group, the aryl group,the heteroaryl group, the aryloxy group, the alkyloxy group, thecycloalkyl group, the heterocycloalkyl group, the arylamine group, thealkylsilyl group, the arylsilyl group, the alkylboron group, thearylboron group, the arylphosphine group, the arylphosphine oxide group,and the arylsilyl group of R₂₁ are each independently unsubstituted orsubstituted with one or more substituents selected from a groupconsisting of deuterium, halogen, a cyano group, a nitro group, a C₁ toC₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, aC₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, aC₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀arylamine group, a C₃ to C₄₀ cycloalkyl group, a heterocycloalkyl grouphaving 3 to 40 nuclear atoms, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀alkylboron group, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphinegroup, a C₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilylgroup.

Further, at least one of the Ar₁ to Ar₅, R₁ to R₈, which do not form thefused ring of Formula 2, and R₉ preferably at least one of the Ar₁ toAr₅ and R₉ may be a substitution product represented by the followingFormula 10 or 11.

In Formulae 10 and 11,

L₃ and L₄ are each a single bond (direct bond), or selected from a groupconsisting of a C₆ to C₁₈ arylene group and a heteroarylene group having5 to 18 nuclear atoms,

Z₆ to Z₈ are the same as or different from each other, and are eachindependently a single bond, or O, S, or N(R₁₆),

provided that a case where Z₆ and Z₇ are all a single bond is excluded,

in this case, when N(R₁₆) is present in plural numbers, a plurality ofN(R₁₆)'s is the same as or different from each other,

R₁₆ is selected from a group consisting of hydrogen, deuterium, halogen,a cyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀alkenyl group, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, aheteroaryl group having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxygroup, a C₁ to C₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, ormay combine with an adjacent group to form a fused ring,

e is an integer of 0 to 3, and when the e is 1 to 3, R₁₂ is selectedfrom a group consisting of deuterium, halogen, a cyano group, a nitrogroup, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀alkynyl group, a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxy group, aC₃ to C₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40nuclear atoms, a C₆ to C₆₀ arylamine group, a C₁ to C₄₀ alkylsilylgroup, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylboron group, a C₆to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxide group, and aC₆ to C₆₀ arylsilyl group,

f, g, and h are an integer of 0 to 4, and when the f, g, and h are eachan integer of 1 to 4, R₁₃ to R₁₅ are selected from a group consisting ofdeuterium, halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C₆ to C₆₀aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group,a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group,and

in this case, the arylene group and the heteroarylene group of L₃ andthe alkyl group, the alkenyl group, the alkynyl group, the aryl group,the heteroaryl group, the aryloxy group, the alkyloxy group, thecycloalkyl group, the heterocycloalkyl group, the arylamine group, thealkylsilyl group, the alkylboron group, the arylboron group, thearylphosphine group, the arylphosphine oxide group, and the arylsilylgroup of R₁₂ to R₁₆ are each independently unsubstituted or substitutedwith one or more substituents selected from a group consisting ofdeuterium, halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C₆ to C₆₀aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀ arylamine group,a C₃ to C₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40nuclear atoms, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group.

In Formula 1, the X₁ may be N(Ar₁). In this case, the Ar₁ is the same asthat defined in Formula 1, and may be preferably a substitution productrepresented by the following Formula 12:

in Formula 12,

L₅ is a single bond, or selected from a group consisting of a C₆ to C₆₀aryl group,

m is an integer of 1 and 2,

A is a 6-membered aromatic ring,

x is an integer of 0 to 2, and when the x is an integer of 1 and 2, R₃₁are selected from a group consisting of deuterium (D), halogen, a cyanogroup, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀ arylgroup, a heteroaryl group having 5 to 60 nuclear atoms, a C₁ to C₄₀alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkylsilyl group,a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, or maycombine with an adjacent group to form a fused ring, and in this case,when the R₃₁ is present in plural numbers, a plurality of R₃₁'s is thesame as or different from each other,

Y₅ to Y₈ are each independently N or C(R₃₆), and in this case, when theC(R₃₆) is present in plural numbers, a plurality of C(R₃₆)'s is the sameas or different from each other,

R₃₂ to R₃₆ are the same as or different from each other, and are eachindependently selected from a group consisting of hydrogen, deuterium(D), halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkyl group, aC₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms,a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms,a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀alkylsilyl group, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, ormay combine with an adjacent group to form a fused ring, and

the alkyl group, the alkenyl group, the alkynyl group, the cycloalkylgroup, the heterocycloalkyl group, the aryl group, the heteroaryl group,the alkyloxy group, the aryloxy group, the alkylsilyl group, thearylsilyl group, the alkylboron group, the arylboron group, thearylphosphine group, the arylphosphine oxide group, and the arylaminegroup of R₃₁ to R₃₆ are each independently unsubstituted or substitutedwith one or more substituents selected from a group consisting ofdeuterium, halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms,a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms,a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀alkylsilyl group, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylamine group,the substituent may combine with an adjacent group to form a fused ring,and in this case, when the substituent is present in plural numbers, thesubstituents are the same as or different from each other.

Specifically, the substitution product represented by Formula 12 may bea substitution product represented by any one of the following Formulae13 to 15.

In Formulae 13 to 15,

L₄, Y₅ to Y₈, and R₃₁ to R₃₅ are each the same as those defined inFormula 12.

The compound of Formula 1 according to the present disclosure may beembodied as the following exemplified compounds, but is not limitedthereto.

The “unsubstituted alkyl” used in the present disclosure means amonovalent functional group obtained by removing a hydrogen atom from alinear or branched, saturated hydrocarbon having 1 to 40 carbon atoms.Non-limiting examples thereof include methyl, ethyl, propyl, isobutyl,sec-butyl, pentyl, iso-amyl, hexyl, and the like.

The “unsubstituted alkenyl” used in the present disclosure means amonovalent functional group obtained by removing a hydrogen atom from alinear or branched, unsaturated hydrocarbon having 2 to 40 carbon atoms,which has one or more carbon-carbon double bonds. Non-limiting examplesthereof include vinyl, allyl, isopropenyl, 2-butenyl, and the like.

The “unsubstituted alkynyl” used in the present disclosure means amonovalent functional group obtained by removing a hydrogen atom from alinear or branched, unsaturated hydrocarbon having 2 to 40 carbon atoms,which has one or more carbon-carbon triple bonds. Non-limiting examplesthereof include ethynyl, 2-propynyl, and the like.

The “unsubstituted cycloalkyl” used in the present disclosure means amonovalent functional group obtained by removing a hydrogen atom from amonocyclic or polycyclic non-aromatic hydrocarbon (saturated cyclichydrocarbon) having 3 to 40 carbon atoms. Non-limiting examples thereofinclude cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, andthe like.

The “unsubstituted heterocycloalkyl” used in the present disclosuremeans a monovalent functional group obtained by removing a hydrogen atomfrom a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3to 40 nuclear atoms, and one or more carbons in the ring, preferably 1to 3 carbons are substituted with a heteroatom such as N, O, Se, or S.Non-limiting examples thereof include morpholine, piperazine, and thelike.

The “unsubstituted aryl” used in the present disclosure means amonovalent functional group obtained by removing a hydrogen atom from anaromatic hydrocarbon having 6 to 60 carbon atoms, in which a single ringor two or more rings are combined. In this case, the two or more ringsmay be simply pendant to each other or pendant to each other in a fusedform. Non-limiting examples thereof include phenyl, biphenyl, terphenyl,naphthyl, phenanthryl, anthryl, and the like.

The “unsubstituted heteroaryl” used in the present disclosure is amonovalent functional group obtained by removing a hydrogen atom from amonoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60nuclear atoms, and one or more carbons in the ring, preferably 1 to 3carbons are substituted with a heteroatom such as nitrogen (N), oxygen(O), sulfur (S), or selenium (Se). In this case, the two or more ringsmay be simply pendant to each other or pendant to each other in a fusedform in the heteroaryl, and furthermore, the heteroaryl may also includea form fused with an aryl group. Non-limiting examples of the heteroarylinclude: a 6-membered monocyclic ring, such as pyridyl, pyrazinyl,pyrimidinyl, pyridazinyl, and triazinyl; a polycyclic ring, such asphenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole,and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl,2-pyrimidinyl, and the like.

The “unsubstituted alkyloxy” used in the present disclosure means amonovalent functional group represented by RO—, and the R is an alkylhaving 1 to 40 carbon atoms, and may include a linear, branched, orcyclic structure. Non-limiting examples of the alkyloxy include methoxy,ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

The “unsubstituted aryloxy” used in the present disclosure means amonovalent functional group represented by R′O—, and the R′ is an arylhaving 6 to 60 carbon atoms. Non-limiting examples of the aryloxyinclude phenyloxy, naphthyloxy, diphenyloxy, and the like.

The “unsubstituted alkylsilyl” used in the present disclosure means asilyl which is substituted with an alkyl having 1 to 40 carbon atoms,the “unsubstituted arylsilyl” means a silyl which is substituted with anaryl having 6 to 60 carbon atoms, the “unsubstituted alkylboron” means aboron which is substituted with an alkyl having 1 to 40 carbon atoms,the “unsubstituted arylboron” means a boron which is substituted with anaryl having 6 to 60 carbon atoms, the “unsubstituted arylphosphine”means a phosphine which is substituted with an aryl having 1 to 60carbon atoms, and the “unsubstituted arylamine” means an amine which issubstituted with an aryl having 6 to 60 carbon atoms.

The “fused ring” used in the present disclosure means a fused aliphaticring, a fused aromatic ring, a fused heteroaliphatic ring, a fusedheteroaromatic ring, or a combined form thereof.

The compound of Formula 1 of the present disclosure may be synthesizedby a general synthesis method (see Chem. Rev., 60:313 (1960); J. Chem.Soc. 4482 (1955); Chem. Rev. 95: 2457 (1995), and the like). Thedetailed synthesis process on the compound of the present disclosurewill be specifically described in Synthesis Examples to be describedbelow.

Meanwhile, the present disclosure provides an organic electroluminescentdevice including the above-described compound represented by Formula 1.

Specifically, the present disclosure includes an anode, a cathode, andone or more organic material layers interposed between the anode and thecathode, and at least one of the organic material layers includes thecompound represented by Formula 1. In this case, the compoundsrepresented by Formula 1 may be used either alone or in mixture of twoor more thereof.

According to an exemplary embodiment of the present disclosure, the oneor more organic material layers include a hole injection layer, a holetransport layer, a light emitting layer, an electron transport layer,and an electron injection layer, and among them, at least one of theorganic material layer includes the compound represented by Formula 1,and preferably, the light emitting layer or the hole transport layer mayinclude the compound represented by Formula 1. In particular, when thecompound represented by Formula 1 is included as a material of lightemitting layer in an organic electroluminescent device, the lightemitting efficiency, luminance, power efficiency, thermal stability, anddevice lifetime of the organic electroluminescent device may beenhanced.

For example, the compound represented by Formula 1 may be aphosphorescent host, a fluorescent host, or a dopant material for alight emitting layer, and may be preferably a phosphorescent host of alight emitting layer.

According to another exemplary embodiment of the present disclosure, theone or more organic material layers include a hole injection layer, ahole transport layer, a light emitting auxiliary layer, a light emittinglayer, an electron transport layer, and an electron injection layer, andin this case, at least one of the organic material layer, preferably alight emitting auxiliary layer may include the compound of Formula 1. Inparticular, when the compound of Formula 1 may be used as a material oflight emitting auxiliary layer for an organic electroluminescent device,the efficiency (light emitting efficiency and power efficiency),lifetime, luminance, driving voltage, and the like of the organicelectroluminescent device may be enhanced.

According to still another exemplary embodiment of the presentdisclosure, the one or more organic material layers include a holeinjection layer, a hole transport layer, a light emitting layer, anelectron transport auxiliary layer, an electron transport layer, and anelectron injection layer, and in this case, at least one of the organicmaterial layer, preferably an electron transport auxiliary layer mayinclude the compound of Formula 1. In particular, when the compound ofFormula 1 may be used as a material of electron transport auxiliarylayer for an organic electroluminescent device, the efficiency (lightemitting efficiency and power efficiency), lifetime, luminance, drivingvoltage, and the like of the organic electroluminescent device may beenhanced.

The structure of the above-described organic electroluminescent deviceof the present disclosure is not particularly limited, and may be, forexample, a structure in which an anode, one or more organic materiallayers, and a cathode are sequentially laminated on a substrate, and aninsulation layer or an adhesive layer is inserted into the interfacebetween the electrode and the organic material layer.

According to an exemplary embodiment, the organic electroluminescentdevice may have a structure in which an anode, a hole injection layer, ahole transport layer, a light emitting layer, an electron transportlayer, and a cathode are sequentially laminated on a substrate.Optionally, a light emitting auxiliary layer may be interposed betweenthe hole transport layer and the light emitting layer. Additionally, anelectron injection layer may also be disposed on the electron transportlayer.

The organic electroluminescent device of the present disclosure may bemanufactured by forming an organic material layer and an electrode usingmaterials and methods known in the art, except that at least one (forexample, a light emitting layer or a light emitting auxiliary layer) ofthe aforementioned organic material layers is formed so as to includethe compound represented by Formula 1.

The organic material layer may be formed by a vacuum deposition methodor a solution application method. Examples of the solution applicationmethod include spin coating, dip coating, doctor blading, inkjetprinting, or a thermal transfer method, but are not limited thereto.

Examples of a substrate which may be used in the present disclosureinclude a silicon wafer, a quartz or glass plate, a metal plate, aplastic film or sheet, and the like, and are not limited thereto.

Alternatively, examples of an anode material include a metal, such asvanadium, chromium, copper, zinc, and gold, or alloys thereof; a metaloxide, such as zinc oxide, indium oxide, indium tin oxide (ITO), andindium zinc oxide (IZO); a combination of metal and oxide, such asZnO:Al or SnO₂:Sb; an electrically conductive polymer, such aspolythiophene, poly(3-methylthiophene),poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, andpolyaniline; or carbon black, and the like, but are not limited thereto.

Further, examples of a cathode material include: a metal, such asmagnesium, calcium, sodium, potassium, titanium, indium, yttrium,lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof;a multi-layer structured material, such as LiF/Al or LiO₂/Al, and thelike, but are not limited thereto.

Further, a material used for a hole injection layer, a hole transportlayer, an electron injection layer, and an electron transport layer isnot particularly limited as long as the material is a typical materialknown in the art.

Hereinafter, the present disclosure will be described in detail throughExamples, but the following Examples only exemplify the presentdisclosure, and the present disclosure is not limited by the followingExamples.

[Preparation Example 1] Synthesis of Compounds Inv1 and Inv2

<Step 1> Synthesis of2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-bromodibenzo[b,e][1,4]dioxine (100 g, 0.38 mol),bis(pinacolato)diboron (115.8 g, 0.46 mol), Pd(dppf)Cl₂ (31 g, 0.038mol), and KOAc (111.9 g, 1.14 mol) were put into a flask, 1,4-dioxane (2L) was added thereto to dissolve the mixture, and then the resultingsolution was heated and stirred for 8 hours. After the reaction wasterminated, distilled water was added thereto, and an organic layer wasextracted with ethyl acetate. The obtained organic layer was dried overNa₂SO₄, distilled under reduced pressure, and then purified with columnchromatography to obtain a compound2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(73 g, yield 62%).

<Step 2> Synthesis of 2-(2-nitrophenyl)dibenzo[b,e][1,4]dioxine

The2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(73 g, 0.235 mol) obtained in <Step 1>, 1-bromo-2-nitrobenzene (57 g,0.282 mol), and Pd(PPh₃)₄ (13.5 g, 0.011 mol) were put into a flask, a 2M saturated aqueous solution of Na₂CO₃ (352 ml) and 1,4-dioxane (2 L)were added thereto to dissolve the mixture, and then the resultingsolution was heated and stirred for 8 hours. After the reaction wasterminated, distilled water was added thereto, and an organic layer wasextracted with ethyl acetate. The obtained organic layer was dried overNa₂SO₄, distilled under reduced pressure, and then purified with columnchromatography to obtain a compound2-(2-nitrophenyl)dibenzo[b,e][1,4]dioxine (65 g, yield 91%).

<Step 3> Synthesis of Compounds Inv1 and Inv2

The 2-(2-nitrophenyl)dibenzo[b,e][1,4]dioxine (65 g, 0.212 mol) obtainedin <Step 2>, triphenylphosphine (PPh₃)(67 g, 0.255 mol), and1,2-dichlorobenzene (1 L) were mixed under nitrogen flow, and then theresulting mixture was stirred for 12 hours. After the reaction wasterminated, 1,2-dichlorobenzene was removed, and an organic layer wasextracted with dichloromethane. The obtained organic layer was driedover Na₂SO₄, distilled under reduced pressure, and then purified withcolumn chromatography to obtain Compound Inv1 (35 g, yield 60%) andCompound Inv2 (12 g, yield 20%).

[Preparation Example 2] Synthesis of Compounds Inv3 and Inv4

<Step 1> Synthesis of2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-bromodibenzo[b,e][1,4]dioxine (100 g, 0.38 mol),bis(pinacolato)diboron (115.8 g, 0.46 mol), Pd(dppf)Cl₂ (31 g, 0.038mol), and KOAc (111.9 g, 1.14 mol) were put into a flask, 1,4-dioxane (2L) was added thereto to dissolve the mixture, and then the resultingsolution was heated and stirred for 8 hours. After the reaction wasterminated, distilled water was added thereto, and an organic layer wasextracted with ethyl acetate. The obtained organic layer was dried overNa₂SO₄, distilled under reduced pressure, and then purified with columnchromatography to obtain a compound2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(73 g, yield 62%).

<Step 2> Synthesis of 2-(5-chloro-2-nitrophenyl)dibenzo[b,e][1,4]dioxine

The2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(73 g, 0.235 mol) obtained in <Step 1>, 2-bromo-4-chloro-1-nitrobenzene(67 g, 0.282 mol), and Pd(PPh₃)₄ (13.5 g, 0.011 mol) were put into aflask, a 2 M saturated aqueous solution of Na₂CO₃ (352 ml) and1,4-dioxane (2 L) were added thereto to dissolve the mixture, and thenthe resulting solution was heated and stirred for 8 hours. After thereaction was terminated, distilled water was added thereto, and anorganic layer was extracted with ethyl acetate. The obtained organiclayer was dried over Na₂SO₄, distilled under reduced pressure, and thenpurified with column chromatography to obtain a compound2-(5-chloro-2-nitrophenyl)dibenzo[b,e][1,4]dioxine (72 g, yield 91%).

<Step 3> Synthesis of Compounds Inv3 and Inv4

The 2-(5-chloro-2-nitrophenyl)dibenzo[b,e][1,4]dioxine (72 g, 0.212 mol)obtained in <Step 2>, triphenylphosphine (67 g, 0.255 mol), and1,2-dichlorobenzene (1 L) were mixed under nitrogen flow, and then theresulting mixture was stirred for 12 hours. After the reaction wasterminated, 1,2-dichlorobenzene was removed, and an organic layer wasextracted with dichloromethane. The obtained organic layer was driedover Na₂SO₄, distilled under reduced pressure, and then purified withcolumn chromatography to obtain Compound Inv3 (35 g, yield 53%) andCompound Inv4 (23 g, yield 35%).

[Preparation Example 3] Synthesis of Compounds Inv5 and Inv6

<Step 1> Synthesis of2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-bromodibenzo[b,e][1,4]dioxine (100 g, 0.38 mol),bis(pinacolato)diboron (115.8 g, 0.46 mol), Pd(dppf)Cl₂ (31 g, 0.038mol), and KOAc (111.9 g, 1.14 mol) were put into a flask, 1,4-dioxane (2L) was added thereto to dissolve the mixture, and then the resultingsolution was heated and stirred for 8 hours. After the reaction wasterminated, distilled water was added thereto, and an organic layer wasextracted with ethyl acetate. The obtained organic layer was dried overNa₂SO₄, distilled under reduced pressure, and then purified with columnchromatography to obtain a compound2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(73 g, yield 62%).

<Step 2> Synthesis of 2-(4-chloro-2-nitrophenyl)dibenzo[b,e][1,4]dioxine

The2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(73 g, 0.235 mol) obtained in <Step 1>, 1-bromo-4-chloro-2-nitrobenzene(67 g, 0.282 mol), and Pd(PPh₃)₄ (13.5 g, 0.011 mol) were put into aflask, a 2 M saturated aqueous solution of Na₂CO₃ (352 ml) and1,4-dioxane (2 L) were added thereto to dissolve the mixture, and thenthe resulting solution was heated and stirred for 8 hours. After thereaction was terminated, distilled water was added thereto, and anorganic layer was extracted with ethyl acetate. The obtained organiclayer was dried over Na₂SO₄, distilled under reduced pressure, and thenpurified with column chromatography to obtain a compound2-(4-chloro-2-nitrophenyl)dibenzo[b,e][1,4]dioxine (72 g, yield 91%).

<Step 3> Synthesis of Compounds Inv5 and Inv6

The 2-(4-chloro-2-nitrophenyl)dibenzo[b,e][1,4]dioxine (72 g, 0.212 mol)obtained in <Step 2>, triphenylphosphine (67 g, 0.255 mol), and1,2-dichlorobenzene (1 L) were mixed under nitrogen flow, and then theresulting mixture was stirred for 12 hours. After the reaction wasterminated, 1,2-dichlorobenzene was removed, and an organic layer wasextracted with dichloromethane. The obtained organic layer was driedover Na₂SO₄, distilled under reduced pressure, and then purified withcolumn chromatography to obtain Compound Inv5 (35 g, yield 53%) andCompound Inv6 (23 g, yield 35%).

[Preparation Example 4] Synthesis of Compounds Inv7 and Inv8

<Step 1> Synthesis of 2-bromo-7-phenyldibenzo[b,e][1,4]dioxine

2,7-dibromodibenzo[b,e][1,4]dioxine (137 g, 0.400 mol), phenylboronicacid (49 g, 0.400 mol), and Pd(dppf)Cl₂ (23.1 g, 0.02 mol) were put intoa flask, a 2 M saturated aqueous solution of Na₂CO₃ (600 ml) and1,4-dioxane (2 L) were added thereto to dissolve the mixture, and thenthe resulting solution was heated and stirred for 8 hours. After thereaction was terminated, distilled water was added thereto, and anorganic layer was extracted with ethyl acetate. The obtained organiclayer was dried over Na₂SO₄, distilled under reduced pressure, and thenpurified with column chromatography to obtain a compound2-bromo-7-phenyldibenzo[b,e][1,4]dioxine (129 g, yield 95%).

<Step 2> Synthesis of4,4,5,5-tetramethyl-2-(7-phenyldibenzo[b,e][1,4]dioxin-2-yl)-1,3,2-dioxaborolane

The 2-bromo-7-phenyldibenzo[b,e][1,4]dioxine (129 g, 0.38 mol) obtainedin <Step 1>, bis(pinacolato)diboron (115.8 g, 0.46 mol), Pd(dppf)Cl₂ (31g, 0.038 mol), and KOAc (111.9 g, 1.14 mol) were put into a flask,1,4-dioxane (2 L) was added thereto to dissolve the mixture, and thenthe resulting solution was heated and stirred for 8 hours. After thereaction was terminated, distilled water was added thereto, and anorganic layer was extracted with ethyl acetate. The obtained organiclayer was dried over Na₂SO₄, distilled under reduced pressure, and thenpurified with column chromatography to obtain a compound4,4,5,5-tetramethyl-2-(7-phenyldibenzo[b,e][1,4]dioxin-2-yl)-1,3,2-dioxaborolane(91 g, yield 62%).

<Step 3> Synthesis of2-(5-chloro-2-nitrophenyl)-7-phenyldibenzo[b,e][1,4]dioxine

The4,4,5,5-tetramethyl-2-(7-phenyldibenzo[b,e][1,4]dioxin-2-yl)-1,3,2-dioxaborolane(91 g, 0.235 mol) obtained in <Step 2>, 2-bromo-4-chloro-1-nitrobenzene(67 g, 0.282 mol), and Pd(PPh₃)₄ (13.5 g, 0.011 mol) were put into aflask, a 2 M saturated aqueous solution of Na₂CO₃ (352 ml) and1,4-dioxane (2 L) were added thereto to dissolve the mixture, and thenthe resulting solution was heated and stirred for 8 hours. After thereaction was terminated, distilled water was added thereto, and anorganic layer was extracted with ethyl acetate. The obtained organiclayer was dried over Na₂SO₄, distilled under reduced pressure, and thenpurified with column chromatography to obtain a compound2-(5-chloro-2-nitrophenyl)-7-phenyldibenzo[b,e][1,4]dioxine (88 g, yield91%).

<Step 4> Synthesis of Compounds Inv7 and Inv8

The 2-(5-chloro-2-nitrophenyl)-7-phenyldibenzo[b,e][1,4]dioxine (88 g,0.212 mol) obtained in <Step 3>, triphenylphosphine (67 g, 0.255 mol),and 1,2-dichlorobenzene (1 L) were mixed under nitrogen flow, and thenthe resulting mixture was stirred for 12 hours. After the reaction wasterminated, 1,2-dichlorobenzene was removed, and an organic layer wasextracted with dichloromethane. The obtained organic layer was driedover Na₂SO₄, distilled under reduced pressure, and then purified withcolumn chromatography to obtain Compound Inv7 (43 g, yield 53%) andCompound Inv8 (28 g, yield 35%).

[Synthesis Example 1] Synthesis of Cpd1

Compound Inv 1 (2.7 g, 10.0 mmol) synthesized in Preparation Example 1and N-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine (5.4 g,12.0 mmol) were dissolved in 100 ml of toluene, and then Pd₂(dba)₃ (0.9g, 1.0 mmol) was introduced thereto under nitrogen. Thereafter, NaOtBu(2.9 g, 30 mmol) was added thereto, (t-Bu)₃P (1.0 ml, 1.0 mmol) wasintroduced into the reaction solution, and then the mixture was refluxedand stirred for 5 hours.

After it was confirmed by TLC that the reaction was terminated, thetemperature was cooled to normal temperature. After the reaction wasterminated, distilled water was added thereto, and an organic layer wasextracted with ethyl acetate. The obtained organic layer was dried overNa₂SO₄, distilled under reduced pressure, and then purified with columnchromatography to obtain Compound Cpd1 (5.5 g, yield 86%).

HRMS [M]⁺: 642.230

[Synthesis Example 2] Synthesis of Cpd2

Compound Cpd2 (5.8 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 1, except that7-bromo-9,9-dimethyl-N-(naphthalen-1-yl)-N-phenyl-9H-fluoren-2-amine(5.9 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 682.262

[Synthesis Example 3] Synthesis of Cpd3

Compound Cpd3 (6.7 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN,N-di([1,1′-biphenyl]-4-yl)-4′-bromo-[1,1′-biphenyl]-4-amine (6.6 g,12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 744.277

[Synthesis Example 4] Synthesis of Cpd4

Compound Cpd4 (6.7 g, yield 81%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN1-([1,1′-biphenyl]-4-yl)-N1-(4′-bromo-[1,1′-biphenyl]-4-yl)-N4,N4-diphenylbenzene-1,4-diamine(7.7 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 835.319

[Synthesis Example 5] Synthesis of Cpd5

Compound Cpd5 (6.9 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN-([1,1′-biphenyl]-4-yl)-N-(4′-bromo-[1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine(7.1 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 784.309

[Synthesis Example 6] Synthesis of Cpd6

Compound Cpd6 (7.0 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN1-(4′-bromo-[1,1′-biphenyl]-4-yl)-N1-(9,9-dimethyl-9H-fluoren-2-yl)-N4,N4-diphenylbenzene-1,4-diamine(8.2 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 875.351

[Synthesis Example 7] Synthesis of Cpd7

Compound Cpd7 (5.7 g, yield 86%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN-([1,1′-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1′-biphenyl]-4-amine (5.7g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 668.246

[Synthesis Example 8] Synthesis of Cpd8

Compound Cpd8 (6.9 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN,N-di([1,1′-biphenyl]-4-yl)-4″-chloro-[1,1′:4′,1″-terphenyl]-4-amine(7.0 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 820.309

[Synthesis Example 9] Synthesis of Cpd12

Compound Cpd12 (6.8 g, yield 80%) was obtained by performing the sameprocess as in Synthesis Example 1, except that4′-chloro-N,N-bis(4-(naphthalen-1-yl)phenyl)-[1,1′-biphenyl]-4-amine(7.3 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 844.309

[Synthesis Example 10] Synthesis of Cpd13

Compound Cpd13 (6.9 g, yield 84%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN-([1,1′-biphenyl]-4-yl)-N-(4-(5-(4-bromophenyl)thiophen-2-yl)phenyl)-[1,1′-biphenyl]-4-amine(7.6 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 826.265

[Synthesis Example 11] Synthesis of Cpd14

Compound Cpd14 (7.0 g, yield 86%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN-([1,1′-biphenyl]-4-yl)-N-(4-(5-(4-chlorophenyl)furan-2-yl)phenyl)-[1,1′-biphenyl]-4-amine(6.9 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 810.288

[Synthesis Example 12] Synthesis of Cpd15

Compound Cpd15 (6.4 g, yield 89%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN,N-di([1,1′-biphenyl]-4-yl)-6-bromonaphthalen-2-amine (6.3 g, 12.0mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 718.262

[Synthesis Example 13] Synthesis of Cpd16

Compound Cpd16 (6.4 g, yield 83%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN-([1,1′-biphenyl]-4-yl)-N-(4′-bromo-[1,1′-biphenyl]-4-yl)phenanthren-9-amine(6.9 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 867.277

[Synthesis Example 14] Synthesis of Cpd17

Compound Cpd17 (6.8 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)phenanthren-2-amine(7.4 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 808.309

[Synthesis Example 15] Synthesis of Cpd18

Compound Cpd18 (6.5 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 1, except thatN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenyl-[1,1′:4′,1″-terphenyl]-4-amine(6.6 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 1.

HRMS [M]⁺: 744.277

[Synthesis Example 16] Synthesis of Cpd22

Compound Inv 2 (2.7 g, 10.0 mmol) synthesized in Preparation Example 1and N-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine (5.4 g,12.0 mmol) were dissolved in toluene (100 ml), and then Pd₂(dba)₃ (0.9g, 1.0 mmol) was introduced thereto under nitrogen. Thereafter, NaOtBu(2.9 g, 30 mmol) was added thereto, (t-Bu)₃P (1.0 ml, 1.0 mmol) wasintroduced into the reaction solution, and then the mixture was refluxedand stirred for 5 hours. After it was confirmed by TLC that the reactionwas terminated, the temperature was cooled to normal temperature. Afterthe reaction was terminated, distilled water was added thereto, and anorganic layer was extracted with ethyl acetate. The obtained organiclayer was dried over Na₂SO₄, distilled under reduced pressure, and thenpurified with column chromatography to obtain Compound Cpd22 (5.5 g,yield 86%).

HRMS [M]⁺: 642.230

[Synthesis Example 17] Synthesis of Cpd23

Compound Cpd23 (5.8 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 16, except that7-bromo-9,9-dimethyl-N-(naphthalen-1-yl)-N-phenyl-9H-fluoren-2-amine(5.9 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 682.262

[Synthesis Example 18] Synthesis of Cpd24

Compound Cpd24 (6.7 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN,N-di([1,1′-biphenyl]-4-yl)-4′-bromo-[1,1′-biphenyl]-4-amine (6.6 g,12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 744.277

[Synthesis Example 19] Synthesis of Cpd25

Compound Cpd25 (6.7 g, yield 81%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN1-([1,1′-biphenyl]-4-yl)-N1-(4′-bromo-[1,1′-biphenyl]-4-yl)-N4,N4-diphenylbenzene-1,4-diamine(7.7 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 835.319

[Synthesis Example 20] Synthesis of Cpd26

Compound Cpd26 (6.9 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN-([1,1′-biphenyl]-4-yl)-N-(4′-bromo-[1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine(7.1 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 784.309

[Synthesis Example 21] Synthesis of Cpd27

Compound Cpd27 (7.0 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN1-(4′-bromo-[1,1′-biphenyl]-4-yl)-N1-(9,9-dimethyl-9H-fluoren-2-yl)-N4,N4-diphenylbenzene-1,4-diamine(8.2 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 875.351

[Synthesis Example 22] Synthesis of Cpd28

Compound Cpd28 (5.7 g, yield 86%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN-([1,1′-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1′-biphenyl]-4-amine (5.7g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 668.246

[Synthesis Example 23] Synthesis of Cpd29

Compound Cpd29 (6.9 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN,N-di([1,1′-biphenyl]-4-yl)-4″-chloro-[1,1′:4′,1″-terphenyl]-4-amine(7.0 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 820.309

[Synthesis Example 24] Synthesis of Cpd33

Compound Cpd33 (6.8 g, yield 80%) was obtained by performing the sameprocess as in Synthesis Example 16, except that4′-chloro-N,N-bis(4-(naphthalen-1-yl)phenyl)-[1,1′-biphenyl]-4-amine(7.3 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 844.309

[Synthesis Example 25] Synthesis of Cpd34

Compound Cpd34 (6.9 g, yield 84%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN-([1,1′-biphenyl]-4-yl)-N-(4-(5-(4-bromophenyl)thiophen-2-yl)phenyl)-[1,1′-biphenyl]-4-amine(7.6 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 826.265

[Synthesis Example 26] Synthesis of Cpd35

Compound Cpd35 (7.0 g, yield 86%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN-([1,1′-biphenyl]-4-yl)-N-(4-(5-(4-chlorophenyl)furan-2-yl)phenyl)-[1,1′-biphenyl]-4-amine(6.9 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 810.288

[Synthesis Example 27] Synthesis of Cpd36

Compound Cpd36 (6.4 g, yield 89%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN,N-di([1,1′-biphenyl]-4-yl)-6-bromonaphthalen-2-amine (6.3 g, 12.0mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 718.262

[Synthesis Example 28] Synthesis of Cpd37

Compound Cpd37 (6.4 g, yield 83%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN-([1,1′-biphenyl]-4-yl)-N-(4′-bromo-[1,1′-biphenyl]-4-yl)phenanthren-9-amine(6.9 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 867.277

[Synthesis Example 29] Synthesis of Cpd38

Compound Cpd38 (6.8 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)phenanthren-2-amine(7.4 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 808.309

[Synthesis Example 30] Synthesis of Cpd39

Compound Cpd39 (6.5 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 16, except thatN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenyl-[1,1′:4′,1″-terphenyl]-4-amine(6.6 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 16.

HRMS [M]⁺: 744.277

[Synthesis Example 31] Synthesis of Cpd19

<Step 1> Synthesis of2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Compound Inv 3 (3.1 g, 10.0 mmol) synthesized in Preparation Example 2and 4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine (4.8 g, 12.0 mmol)were dissolved in toluene (100 ml), and then Pd₂(dba)₃ (0.9 g, 1.0 mmol)was introduced thereto under nitrogen. Thereafter, NaOtBu (2.9 g, 30mmol) was added thereto, (t-Bu)₃P (1.0 ml, 1.0 mmol) was introduced intothe reaction solution, and then the mixture was refluxed and stirred for5 hours.

After it was confirmed by TLC that the reaction was terminated, thetemperature was cooled to normal temperature. After the reaction wasterminated, distilled water was added thereto, and an organic layer wasextracted with ethyl acetate. The obtained organic layer was dried overNa₂SO₄, distilled under reduced pressure, and then purified with columnchromatography to obtain a compound4′-(2-chloro-5H-benzo[5,6][1,4]dioxino[2,3-b]carbazol-5-yl)-N,N-diphenyl-[1,1′-biphenyl]-4-amine(4.8 g, yield 77%).

<Step 2> Synthesis of Cpd19

The4′-(2-chloro-5H-benzo[5,6][1,4]dioxino[2,3-b]carbazol-5-yl)-N,N-diphenyl-[1,1′-biphenyl]-4-amine(4.8 g, 7.70 mmol) obtained in <Step 1>, phenylboronic acid (1.18 g,9.67 mmol), NaOH (1.06 g, 26.4 mmol), and THF/H₂O (100 ml/50 ml) wereput into a flask, and the resulting mixture was stirred. Thereafter,Pd(PPh₃)₄ (5 mol %, 0.51 g) was added thereto at 40° C., and theresulting mixture was stirred at 80° C. for 12 hours.

After it was confirmed by TLC that the reaction was terminated, thetemperature was cooled to normal temperature. After the reaction wasterminated, distilled water was added thereto, and an organic layer wasextracted with ethyl acetate. The obtained organic layer was dried overNa₂SO₄, distilled under reduced pressure, and then purified with columnchromatography to obtain Compound Cpd19 (4.1 g, yield 80%).

HRMS [M]⁺: 668.246

[Synthesis Example 32] Synthesis of Cpd21

Compound Cpd21 (5.3 g, yield 64%) was obtained by performing the sameprocess as in Synthesis Example 31, except thatN,N-di([1,1′-biphenyl]-4-yl)-4′-bromo-[1,1′-biphenyl]-4-amine (6.6 g,12.0 mmol) was used instead of4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine used in Synthesis Example31.

HRMS [M]⁺: 820.309

[Synthesis Example 33] Synthesis of Cpd40

Compound Cpd40 (4.1 g, yield 65%) was obtained by performing the sameprocess as in Synthesis Example 31, except that Compound Inv 4 (3.1 g,10.0 mmol) synthesized in Preparation Example 2 was used instead ofCompound Inv 3 used in Synthesis Example 31.

HRMS [M]⁺: 668.246

[Synthesis Example 34] Synthesis of Cpd42

Compound Cpd42 (4.9 g, yield 60%) was obtained by performing the sameprocess as in Synthesis Example 32, except that Compound Inv 4 (3.1 g,10.0 mmol) synthesized in Preparation Example 2 was used instead ofCompound Inv 3 used in Synthesis Example 32.

HRMS [M]⁺: 820.309

[Synthesis Example 35] Synthesis of Cpd46

Compound Cpd46 (4.5 g, yield 60%) was obtained by performing the sameprocess as in Synthesis Example 31, except that iodobenzene (2.4 g, 12.0mmol) andN-([1,1′-biphenyl]-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1′-biphenyl]-4-amine(5.1 g, 9.67 mmol) were used instead of4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine and phenylboronic acidused in Synthesis Example 31, respectively.

HRMS [M]⁺: 744.277

[Synthesis Example 36] Synthesis of Cpd47

Compound Cpd47 (4.5 g, yield 58%) was obtained by performing the sameprocess as in Synthesis Example 31, except that iodobenzene (2.4 g, 12.0mmol) andN-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-fluoren-2-amine(5.4 g, 9.67 mmol) were used instead of4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine and phenylboronic acidused in Synthesis Example 31, respectively.

HRMS [M]⁺: 784.309

[Synthesis Example 37] Synthesis of Cpd49

Compound Cpd49 (5.2 g, yield 63%) was obtained by performing the sameprocess as in Synthesis Example 31, except that iodobenzene (2.4 g, 12.0mmol) andN,N-di([1,1′-biphenyl]-4-yl)-4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-4-amine(5.8 g, 9.67 mmol) were used instead of4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine and phenylboronic acidused in Synthesis Example 31, respectively.

HRMS [M]⁺: 820.309

[Synthesis Example 38] Synthesis of Cpd51

Compound Cpd51 (5.6 g, yield 68%) was obtained by performing the sameprocess as in Synthesis Example 31, except that 4-bromo-1,1′-biphenyl(2.8 g, 12.0 mmol) andN-([1,1′-biphenyl]-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1′-biphenyl]-4-amine(5.1 g, 9.67 mmol) were used instead of4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine and phenylboronic acidused in Synthesis Example 31, respectively.

HRMS [M]⁺: 820.309

[Synthesis Example 39] Synthesis of Cpd52

Compound Cpd52 (4.6 g, yield 57%) was obtained by performing the sameprocess as in Synthesis Example 31, except that iodobenzene (2.4 g, 12.0mmol) andN-(9,9-dimethyl-9H-fluoren-2-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phenanthren-2-amine(5.7 g, 9.67 mmol) were used instead of4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine and phenylboronic acidused in Synthesis Example 31, respectively.

HRMS [M]⁺: 808.309

[Synthesis Example 40] Synthesis of Cpd54

Compound Cpd54 (4.5 g, yield 60%) was obtained by performing the sameprocess as in Synthesis Example 35, except that Compound Inv 5 (3.1 g,10.0 mmol) synthesized in Preparation Example 3 was used instead ofCompound Inv 3 used in Synthesis Example 35.

HRMS [M]⁺: 744.277

[Synthesis Example 41] Synthesis of Cpd55

Compound Cpd55 (4.5 g, yield 58%) was obtained by performing the sameprocess as in Synthesis Example 36, except that Compound Inv 5 (3.1 g,10.0 mmol) synthesized in Preparation Example 3 was used instead ofCompound Inv 3 used in Synthesis Example 36.

HRMS [M]⁺: 784.309

[Synthesis Example 42] Synthesis of Cpd57

Compound Cpd57 (5.2 g, yield 63%) was obtained by performing the sameprocess as in Synthesis Example 37, except that Compound Inv 5 (3.1 g,10.0 mmol) synthesized in Preparation Example 3 was used instead ofCompound Inv 3 used in Synthesis Example 37.

HRMS [M]⁺: 820.309

[Synthesis Example 43] Synthesis of Cpd60

Compound Cpd60 (4.6 g, yield 57%) was obtained by performing the sameprocess as in Synthesis Example 39, except that Compound Inv 5 (3.1 g,10.0 mmol) synthesized in Preparation Example 3 was used instead ofCompound Inv 3 used in Synthesis Example 39.

HRMS [M]⁺: 808.309

[Synthesis Example 44] Synthesis of Cpd70

Compound Cpd70 (4.5 g, yield 60%) was obtained by performing the sameprocess as in Synthesis Example 35, except that Compound Inv 4 (3.1 g,10.0 mmol) synthesized in Preparation Example 2 was used instead ofCompound Inv 3 used in Synthesis Example 35.

HRMS [M]⁺: 744.277

[Synthesis Example 45] Synthesis of Cpd71

Compound Cpd71 (4.5 g, yield 58%) was obtained by performing the sameprocess as in Synthesis Example 36, except that Compound Inv 4 (3.1 g,10.0 mmol) synthesized in Preparation Example 2 was used instead ofCompound Inv 3 used in Synthesis Example 36.

HRMS [M]⁺: 784.309

[Synthesis Example 46] Synthesis of Cpd73

Compound Cpd73 (5.2 g, yield 63%) was obtained by performing the sameprocess as in Synthesis Example 37, except that Compound Inv 4 (3.1 g,10.0 mmol) synthesized in Preparation Example 2 was used instead ofCompound Inv 3 used in Synthesis Example 37.

HRMS [M]⁺: 820.309

[Synthesis Example 47] Synthesis of Cpd75

Compound Cpd75 (5.6 g, yield 68%) was obtained by performing the sameprocess as in Synthesis Example 38, except that Compound Inv 4 (3.1 g,10.0 mmol) synthesized in Preparation Example 2 was used instead ofCompound Inv 3 used in Synthesis Example 38.

HRMS [M]⁺: 820.309

[Synthesis Example 48] Synthesis of Cpd76

Compound Cpd76 (4.6 g, yield 57%) was obtained by performing the sameprocess as in Synthesis Example 39, except that Compound Inv 4 (3.1 g,10.0 mmol) synthesized in Preparation Example 2 was used instead ofCompound Inv 3 used in Synthesis Example 39.

HRMS [M]⁺: 808.309

[Synthesis Example 49] Synthesis of Cpd77

Compound Cpd77 (4.5 g, yield 60%) was obtained by performing the sameprocess as in Synthesis Example 35, except that Compound Inv 6 (3.1 g,10.0 mmol) synthesized in Preparation Example 3 was used instead ofCompound Inv 3 used in Synthesis Example 35.

HRMS [M]⁺: 744.277

[Synthesis Example 50] Synthesis of Cpd78

Compound Cpd78 (4.5 g, yield 58%) was obtained by performing the sameprocess as in Synthesis Example 36, except that Compound Inv 6 (3.1 g,10.0 mmol) synthesized in Preparation Example 3 was used instead ofCompound Inv 3 used in Synthesis Example 36.

HRMS [M]⁺: 784.309

[Synthesis Example 51] Synthesis of Cpd80

Compound Cpd80 (5.2 g, yield 63%) was obtained by performing the sameprocess as in Synthesis Example 37, except that Compound Inv 6 (3.1 g,10.0 mmol) synthesized in Preparation Example 3 was used instead ofCompound Inv 3 used in Synthesis Example 37.

HRMS [M]⁺: 820.309

[Synthesis Example 52] Synthesis of Cpd81

Compound Cpd81 (4.6 g, yield 57%) was obtained by performing the sameprocess as in Synthesis Example 39, except that Compound Inv 6 (3.1 g,10.0 mmol) synthesized in Preparation Example 3 was used instead ofCompound Inv 3 used in Synthesis Example 39.

HRMS [M]⁺: 808.309

[Synthesis Example 53] Synthesis of Cpd20

Compound Cpd20 (4.6 g, yield 65%) was obtained by performing the sameprocess as in Synthesis Example 31, except that Compound Inv 7 (3.8 g,10.0 mmol) andN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine (5.4 g,12.0 mmol) synthesized in Preparation Example 4 were used instead ofCompound Inv 3 and 4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine used inSynthesis Example 31, respectively.

HRMS [M]⁺: 794.293

[Synthesis Example 54] Synthesis of Cpd41

Compound Cpd41 (4.6 g, yield 65%) was obtained by performing the sameprocess as in Synthesis Example 53, except that Compound Inv 8 (3.8 g,10.0 mmol) synthesized in Preparation Example 4 was used instead of Inv7 used in Synthesis Example 31.

HRMS [M]⁺: 794.293

[Synthesis Example 55] Synthesis of Cpd48

<Step 1> Synthesis of2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Compound Inv 3 (3.1 g, 10.0 mmol) synthesized in Preparation Example 2and iodobenzene (2.5 g, 12.0 mmol) were dissolved in toluene (100 ml),and then Pd₂(dba)₃ (0.9 g, 1.0 mmol) was introduced thereto undernitrogen. Thereafter, NaOtBu (2.9 g, 30 mmol) was added thereto,(t-Bu)₃P (1.0 ml, 1.0 mmol) was introduced into the reaction solution,and then the mixture was refluxed and stirred for 5 hours.

After it was confirmed by TLC that the reaction was terminated, thetemperature was cooled to normal temperature. After the reaction wasterminated, distilled water was added thereto, and an organic layer wasextracted with ethyl acetate. The obtained organic layer was dried overNa₂SO₄, distilled under reduced pressure, and then purified with columnchromatography to obtain2-chloro-5-phenyl-5H-benzo[5,6][1,4]dioxino[2,3-b]carbazole (3.3 g,yield 83%).

<Step 2> Synthesis of Cpd48

The 2-chloro-5-phenyl-5H-benzo[5,6][1,4]dioxino[2,3-b]carbazole (3.3 g,8.5 mmol) obtained in <Step 1> andN-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (3.7 g, 10.2mmol) were dissolved in toluene (85 ml), and then Pd₂(dba)₃ (0.76 g, 0.8mmol) was introduced thereinto under nitrogen. Thereafter, NaOtBu (2.4g, 25 mmol) was added thereto, (t-Bu)₃P (0.8 ml, 0.8 mmol) wasintroduced into the reaction solution, and then the mixture was refluxedand stirred for 5 hours.

After it was confirmed by TLC that the reaction was terminated, thetemperature was cooled to normal temperature. After the reaction wasterminated, distilled water was added thereto, and an organic layer wasextracted with ethyl acetate. The obtained organic layer was dried overNa₂SO₄, distilled under reduced pressure, and then purified with columnchromatography to obtain Compound Cpd48 (4.8 g, yield 80%).

HRMS [M]⁺: 708.277

[Synthesis Example 56] Synthesis of Cpd56

Compound Cpd56 (4.6 g, yield 65%) was obtained by performing the sameprocess as in Synthesis Example 55, except that Compound Inv 5 (3.1 g,10.0 mmol) synthesized in Preparation Example 3 was used instead ofCompound Inv 3 used in Synthesis Example 55.

HRMS [M]⁺: 708.277

[Synthesis Example 57] Synthesis of Cpd72

Compound Cpd72 (4.3 g, yield 61%) was obtained by performing the sameprocess as in Synthesis Example 55, except that Compound Inv 4 (3.1 g,10.0 mmol) synthesized in Preparation Example 3 was used instead ofCompound Inv 3 used in Synthesis Example 55.

HRMS [M]⁺: 708.277

[Synthesis Example 58] Synthesis of Cpd79

Compound Cpd79 (4.2 g, yield 60%) was obtained by performing the sameprocess as in Synthesis Example 55, except that Compound Inv 6 (3.1 g,10.0 mmol) synthesized in Preparation Example 3 was used instead ofCompound Inv 3 used in Synthesis Example 55.

HRMS [M]⁺: 708.277

[Synthesis Example 59] Synthesis of Cpd86

Compound Inv 1 (2.7 g, 10.0 mmol) synthesized in Preparation Example 1,2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.0 mmol), NaH (0.24 g,10.0 mmol), and DMF (50 ml) were mixed, and the resulting mixture wasstirred at normal temperature for 1 hour. After the reaction wasterminated, water was added thereto, and a solid product was filteredand then purified with column chromatography to obtain Compound Cpd86(4.7 g, yield 93%).

HRMS [M]⁺: 504.158

[Synthesis Example 60] Synthesis of Cpd87

Compound Cpd87 (4.3 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 59, except that2-chloro-4,6-diphenylpyridine (2.6 g, 10.0 mmol) was used instead of2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 59.

HRMS [M]⁺: 502.168

[Synthesis Example 61] Synthesis of Cpd88

Compound Cpd88 (4.4 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 59, except that4-bromo-2,6-diphenylpyrimidine (3.1 g, 10.0 mmol) was used instead of2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 59.

HRMS [M]⁺: 503.163

[Synthesis Example 62] Synthesis of Cpd89

Compound Cpd89 (4.5 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 59, except that2-bromo-4,6-diphenylpyrimidine (3.1 g, 10.0 mmol) was used instead of2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 59.

HRMS [M]⁺: 503.163

[Synthesis Example 63] Synthesis of Cpd128

Compound Cpd128 (4.5 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 59, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 59.

HRMS [M]⁺: 504.158

[Synthesis Example 64] Synthesis of Cpd129

Compound Cpd129 (4.3 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 60, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 60.

HRMS [M]⁺: 502.168

[Synthesis Example 65] Synthesis of Cpd130

Compound Cpd130 (4.4 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 61, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 61.

HRMS [M]⁺: 503.163

[Synthesis Example 66] Synthesis of Cpd131

Compound Cpd131 (4.5 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 62, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 62.

HRMS [M]⁺: 503.163

[Synthesis Example 67] Synthesis of Cpd90

Compound Inv 1 (2.7 g, 10.0 mmol) synthesized in Preparation Example 1and 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (4.7 g, 12.0 mmol)were dissolved in toluene (100 ml), and then Pd2(dba)3 (0.9 g, 1.0 mmol)was introduced thereto under nitrogen. Thereafter, NaOtBu (2.9 g, 30mmol) was added thereto, (t-Bu)3P (1.0 ml, 1.0 mmol) was introduced intothe reaction solution, and then the mixture was refluxed and stirred for5 hours.

After it was confirmed by TLC that the reaction was terminated, thetemperature was cooled to normal temperature. After the reaction wasterminated, distilled water was added thereto, and an organic layer wasextracted with ethyl acetate. The obtained organic layer was dried overNa2SO4, distilled under reduced pressure, and then purified with columnchromatography to obtain Compound Cpd90 (4.9 g, yield 84%).

HRMS [M]⁺: 580.189

[Synthesis Example 68] Synthesis of Cpd91

Compound Cpd91 (5.1 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 67, except that2-(4-bromophenyl)-4,6-diphenylpyrimidine (4.6 g, 12.0 mmol) was usedinstead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used inSynthesis Example 67.

HRMS [M]⁺: 579.194

[Synthesis Example 69] Synthesis of Cpd92

Compound Cpd92 (5.2 g, yield 90%) was obtained by performing the sameprocess as in Synthesis Example 67, except that2-(4-bromophenyl)-4,6-diphenylpyridine (4.6 g, 12.0 mmol) was usedinstead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used inSynthesis Example 67.

HRMS [M]+: 578.199

[Synthesis Example 70] Synthesis of Cpd93

Compound Cpd93 (4.9 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 67, except that4-(4-bromophenyl)-2,6-diphenylpyrimidine (4.6 g, 12.0 mmol) was usedinstead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used inSynthesis Example 67.

HRMS [M]⁺: 579.194

[Synthesis Example 71] Synthesis of Cpd94

Compound Cpd94 (5.2 g, yield 90%) was obtained by performing the sameprocess as in Synthesis Example 67, except that2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (4.6 g, 12.0 mmol) wasused instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used inSynthesis Example 67.

HRMS [M]⁺: 580.189

[Synthesis Example 72] Synthesis of Cpd95

Compound Cpd95 (4.7 g, yield 82%) was obtained by performing the sameprocess as in Synthesis Example 67, except that2-(3-bromophenyl)-4,6-diphenylpyridine (4.6 g, 12.0 mmol) was usedinstead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used inSynthesis Example 67.

HRMS [M]⁺: 578.199

[Synthesis Example 73] Synthesis of Cpd96

Compound Cpd96 (5.1 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 67, except that4-(3-bromophenyl)-2,6-diphenylpyrimidine (4.6 g, 12.0 mmol) was usedinstead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used inSynthesis Example 67.

HRMS [M]⁺: 579.194

[Synthesis Example 74] Synthesis of Cpd97

Compound Cpd97 (5.3 g, yield 91%) was obtained by performing the sameprocess as in Synthesis Example 67, except that2-(3-bromophenyl)-4,6-diphenylpyrimidine (4.6 g, 12.0 mmol) was usedinstead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used inSynthesis Example 67.

HRMS [M]⁺: 579.194

[Synthesis Example 75] Synthesis of Cpd100

Compound Cpd100 (6.1 g, yield 83%) was obtained by performing the sameprocess as in Synthesis Example 67, except that2,4-di([1,1′-biphenyl]-4-yl)-6-(4-bromophenyl)-1,3,5-triazine (6.5 g,12.0 mmol) was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example67.

HRMS [M]⁺: 732.252

[Synthesis Example 76] Synthesis of Cpd101

Compound Cpd101 (5.2 g, yield 80%) was obtained by performing the sameprocess as in Synthesis Example 67, except that2-(5-bromo-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (5.6 g,12.0 mmol) was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example67.

HRMS [M]⁺: 656.221

[Synthesis Example 77] Synthesis of Cpd105

Compound Cpd105 (4.8 g, yield 83%) was obtained by performing the sameprocess as in Synthesis Example 67, except that2-(3-bromophenyl)triphenylene (4.6 g, 12.0 mmol) was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example67.

HRMS [M]⁺: 575.188

[Synthesis Example 78] Synthesis of Cpd106

Compound Cpd106 (4.9 g, yield 81%) was obtained by performing the sameprocess as in Synthesis Example 67, except that4-(4-bromophenyl)-6-phenyldibenzo[b,d]thiophene (5.0 g, 12.0 mmol) wasused instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used inSynthesis Example 67.

HRMS [M]⁺: 607.160

[Synthesis Example 79] Synthesis of Cpd110

Compound Cpd110 (4.8 g, yield 93%) was obtained by performing the sameprocess as in Synthesis Example 67, except that3-bromo-9-phenyl-9H-carbazole (3.9 g, 12.0 mmol) was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example67.

HRMS [M]⁺: 514.618

[Synthesis Example 80] Synthesis of Cpd111

Compound Cpd111 (3.6 g, yield 82%) was obtained by performing the sameprocess as in Synthesis Example 67, except that 4-bromodibenzo[b,d]furan(3.0 g, 12.0 mmol) was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example67.

HRMS [M]⁺: 439.120

[Synthesis Example 81] Synthesis of Cpd112

Compound Cpd112 (3.6 g, yield 80%) was obtained by performing the sameprocess as in Synthesis Example 67, except that4-bromodibenzo[b,d]thiophene (3.2 g, 12.0 mmol) was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example67.

HRMS [M]⁺: 455.098

[Synthesis Example 82] Synthesis of Cpd113

Compound Cpd113 (3.9 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 67, except that 2-bromodibenzo[b,d]furan(3.0 g, 12.0 mmol) was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example67.

HRMS [M]⁺: 439.120

[Synthesis Example 83] Synthesis of Cpd114

Compound Cpd114 (4.1 g, yield 89%) was obtained by performing the sameprocess as in Synthesis Example 67, except that2-bromodibenzo[b,d]thiophene (3.2 g, 12.0 mmol) was used instead of2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example67.

HRMS [M]⁺: 455.098

[Synthesis Example 84] Synthesis of Cpd115

<Step 1> Synthesis of 3-bromo-9-tosyl-9H-carbazole

Acetone (200 mL) was put into KOH (2.7 g, 48 mmol) to dissolve KOH, andthen 3-bromo-9H-carbazole (9.8 g, 40 mmol) was introduced thereinto.Thereafter, TsCl (8.4 g, 44 mmol) was added thereto, the mixture wasrefluxed for 3 hours, and then cooled, and 1 L of iced water was pouredtherein under stirring. After being stirred for 30 minutes, the mixturewas filtered to obtain a crude product. Thereafter, the crude productwas recrystallized from CH₂Cl2/EtOH, and then3-bromo-9-tosyl-9H-carbazole (9.8 g, yield 61%) was obtained.

<Step 2> Synthesis of5-(9-tosyl-9H-carbazol-3-yl)-5H-benzo[5,6][1,4]dioxino[2,3-b]carbazole

The 3-bromo-9-tosyl-9H-carbazole (9.6 g, 24 mmol) obtained in <Step 1>,Compound Inv 1 (7.9 g, 29 mmol) synthesized in Preparation Example 1,CuI (0.4 g, 2.0 mmol), 1,2-diaminocyclohexane (0.3 g, 2.4 mmol),K₃PO₄—H₂O (10.6 g, 50 mmol), and toluene (150 ml) were added to a 500 mLround flask. The reactants were heated under reflux, and stirred undernitrogen atmosphere for 24 hours. After it was confirmed by TLC that thereaction was terminated, the temperature was cooled to normaltemperature. After the reaction was terminated, distilled water wasadded thereto, and an organic layer was extracted with ethyl acetate.The obtained organic layer was dried over Na₂SO₄, distilled underreduced pressure, and then purified with column chromatography to obtaina compound5-(9-tosyl-9H-carbazol-3-yl)-5H-benzo[5,6][1,4]dioxino[2,3-b]carbazole(12.4 g, yield 87%).

<Step 3> Synthesis of5-(9H-carbazol-3-yl)-5H-benzo[5,6][1,4]dioxino[2,3-b]carbazole

The5-(9-tosyl-9H-carbazol-3-yl)-5H-benzo[5,6][1,4]dioxino[2,3-b]carbazole(12.4 g, 21 mmol) obtained in <Step 2>, NaOH (8.0 g, 200 mmol), THF (80ml), MeOH (40 ml), and water (40 ml) were added to a 500 ml-round flask,and then the reactants were heated under reflux for 12 hours. After itwas confirmed by TLC that the reaction was terminated, the temperaturewas cooled to normal temperature. After the reaction was terminated,distilled water was added thereto, and an organic layer was extractedwith ethyl acetate. The obtained organic layer was dried over Na₂SO₄,distilled under reduced pressure, and then purified with columnchromatography to obtain5-(9H-carbazol-3-yl)-5H-benzo[5,6][1,4]dioxino[2,3-b]carbazole (8.4 g,yield 91%).

<Step 4> Synthesis of Cpd115

The 5-(9H-carbazol-3-yl)-5H-benzo[5,6][1,4]dioxino[2,3-b]carbazole (3.0g, 7 mmol) obtained in <Step 3>, 2-bromodibenzo thiophene (3.0 g, 10mmol), Pd₂(dba)₃ (0.5 g, 0.5 mmol), S-Phos (0.8 g, 2.0 mmol), NaOtBu(2.9 g, 30 mmol), and 200 ml of xylene were added to a 500 ml-roundflask, and the reactants were heated under reflux and stirred undernitrogen atmosphere for 12 hours. After it was confirmed by TLC that thereaction was terminated, the temperature was cooled to normaltemperature. After the reaction was terminated, distilled water wasadded thereto, and an organic layer was extracted with ethyl acetate.The obtained organic layer was dried over Na₂SO₄, distilled underreduced pressure, and then purified with column chromatography to obtainCompound Cpd115 (5.2 g, yield 84%).

HRMS [M]+: 620.155

[Synthesis Example 85] Synthesis of Cpd116

Compound Cpd116 (5.9 g, yield 87%) was obtained by performing the sameprocess as in Synthesis Example 84, except that3-bromo-9-phenyl-9H-carbazole (3.2 g, 10 mmol) was used instead of2-bromodibenzo thiophene used in Synthesis Example 84.

HRMS [M]⁺: 679.226

[Synthesis Example 86] Synthesis of Cpd117

Compound Cpd117 (5.4 g, yield 90%) was obtained by performing the sameprocess as in Synthesis Example 84, except that 2-bromodibenzo[b,d]furan(2.5 g, 10 mmol) was used instead of 2-bromodibenzo thiophene used inSynthesis Example 84.

HRMS [M]⁺: 604.178

[Synthesis Example 87] Synthesis of Cpd118

Compound Cpd118 (5.6 g, yield 83%) was obtained by performing the sameprocess as in Synthesis Example 84, except that2-chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10 mmol) was used insteadof 2-bromodibenzo thiophene used in Synthesis Example 84.

HRMS [M]⁺: 669.216

[Synthesis Example 88] Synthesis of Cpd119

Compound Cpd119 (4.2 g, yield 64%) was obtained by performing the sameprocess as in Synthesis Example 31, except that2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (4.7 g, 12.0 mmol) wasused instead of 4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine used inSynthesis Example 31.

HRMS [M]⁺: 656.221

[Synthesis Example 89] Synthesis of Cpd120

Compound Cpd120 (3.9 g, yield 60%) was obtained by performing the sameprocess as in Synthesis Example 31, except that2-(3-bromophenyl)-4,6-diphenylpyridine (4.6 g, 12.0 mmol) was usedinstead of 4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine used inSynthesis Example 31.

HRMS [M]⁺: 654.230

[Synthesis Example 90] Synthesis of Cpd121

Compound Cpd121 (4.4 g, yield 68%) was obtained by performing the sameprocess as in Synthesis Example 31, except that4-(3-bromophenyl)-2,6-diphenylpyrimidine (4.7 g, 12.0 mmol) was usedinstead of 4′-bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine used inSynthesis Example 31.

HRMS [M]⁺: 655.226

[Synthesis Example 91] Synthesis of Cpd122

Compound Cpd122 (4.0 g, yield 60%) was obtained by performing the sameprocess as in Synthesis Example 53, except that2-chloro-4,6-diphenyl-1,3,5-triazine (3.2 g, 12.0 mmol) was used insteadof N-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 53.

HRMS [M]⁺: 656.221

[Synthesis Example 92] Synthesis of Cpd123

Compound Cpd123 (4.0 g, yield 62%) was obtained by performing the sameprocess as in Synthesis Example 53, except that4-chloro-2,6-diphenylpyrimidine (3.2 g, 12.0 mmol) was used instead ofN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-2-amine used inSynthesis Example 53.

HRMS [M]⁺: 655.226

[Synthesis Example 93] Synthesis of Cpd132

Compound Cpd132 (4.9 g, yield 84%) was obtained by performing the sameprocess as in Synthesis Example 67, except that Compound Inv 2synthesized in Preparation Example 1 was used instead of Compound Inv 1used in Synthesis Example 67.

HRMS [M]⁺: 580.189

[Synthesis Example 94] Synthesis of Cpd133

Compound Cpd133 (5.1 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 68, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 68.

HRMS [M]⁺: 579.194

[Synthesis Example 95] Synthesis of Cpd134

Compound Cpd134 (5.2 g, yield 90%) was obtained by performing the sameprocess as in Synthesis Example 69, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 69.

HRMS [M]⁺: 578.199

[Synthesis Example 96] Synthesis of Cpd135

Compound Cpd135 (4.9 g, yield 85%) was obtained by performing the sameprocess as in Synthesis Example 70, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 70.

HRMS [M]⁺: 579.194

[Synthesis Example 97] Synthesis of Cpd136

Compound Cpd136 (5.2 g, yield 90%) was obtained by performing the sameprocess as in Synthesis Example 71, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 71.

HRMS [M]⁺: 580.189

[Synthesis Example 98] Synthesis of Cpd137

Compound Cpd137 (4.7 g, yield 82%) was obtained by performing the sameprocess as in Synthesis Example 72, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 72.

HRMS [M]⁺: 578.199

[Synthesis Example 99] Synthesis of Cpd138

Compound Cpd138 (5.1 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 73, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 73.

HRMS [M]⁺: 579.194

[Synthesis Example 100] Synthesis of Cpd139

Compound Cpd139 (5.3 g, yield 91%) was obtained by performing the sameprocess as in Synthesis Example 74, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 74.

HRMS [M]⁺: 579.194

[Synthesis Example 101] Synthesis of Cpd142

Compound Cpd142 (6.1 g, yield 83%) was obtained by performing the sameprocess as in Synthesis Example 75, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 75.

HRMS [M]⁺: 732.252

[Synthesis Example 102] Synthesis of Cpd143

Compound Cpd143 (5.2 g, yield 80%) was obtained by performing the sameprocess as in Synthesis Example 76, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 76.

HRMS [M]⁺: 656.221

[Synthesis Example 103] Synthesis of Cpd147

Compound Cpd147 (4.8 g, yield 83%) was obtained by performing the sameprocess as in Synthesis Example 77, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 77.

HRMS [M]⁺: 575.188

[Synthesis Example 104] Synthesis of Cpd148

Compound Cpd148 (4.9 g, yield 81%) was obtained by performing the sameprocess as in Synthesis Example 78, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 78.

HRMS [M]⁺: 607.160

[Synthesis Example 105] Synthesis of Cpd152

Compound Cpd152 (4.8 g, yield 93%) was obtained by performing the sameprocess as in Synthesis Example 79, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 79.

HRMS [M]⁺: 514.618

[Synthesis Example 106] Synthesis of Cpd153

Compound Cpd153 (3.6 g, yield 82%) was obtained by performing the sameprocess as in Synthesis Example 80, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 80.

HRMS [M]⁺: 439.120

[Synthesis Example 107] Synthesis of Cpd154

Compound Cpd154 (3.6 g, yield 80%) was obtained by performing the sameprocess as in Synthesis Example 81, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 81.

HRMS [M]⁺: 455.098

[Synthesis Example 108] Synthesis of Cpd155

Compound Cpd155 (3.9 g, yield 88%) was obtained by performing the sameprocess as in Synthesis Example 82, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 82.

HRMS [M]⁺: 439.120

[Synthesis Example 109] Synthesis of Cpd156

Compound Cpd156 (4.1 g, yield 89%) was obtained by performing the sameprocess as in Synthesis Example 83, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 83.

HRMS [M]⁺: 455.098

[Synthesis Example 110] Synthesis of Cpd157

Compound Cpd157 (5.2 g, yield 84%) was obtained by performing the sameprocess as in Synthesis Example 84, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 84.

HRMS [M]⁺: 620.155

[Synthesis Example 111] Synthesis of Cpd158

Compound Cpd158 (5.9 g, yield 87%) was obtained by performing the sameprocess as in Synthesis Example 85, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 85.

HRMS [M]⁺: 679.226

[Synthesis Example 112] Synthesis of Cpd159

Compound Cpd159 (5.4 g, yield 90%) was obtained by performing the sameprocess as in Synthesis Example 86, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 86.

HRMS [M]⁺: 604.178

[Synthesis Example 113] Synthesis of Cpd160

Compound Cpd160 (5.6 g, yield 83%) was obtained by performing the sameprocess as in Synthesis Example 87, except that Compound Inv 2 (2.7 g,10.0 mmol) synthesized in Preparation Example 1 was used instead ofCompound Inv 1 used in Synthesis Example 87.

HRMS [M]⁺: 669.216

[Synthesis Example 114] Synthesis of Cpd161

Compound Cpd119 (4.2 g, yield 64%) was obtained by performing the sameprocess as in Synthesis Example 88, except that Compound Inv 4 (3.1 g,10.0 mmol) synthesized in Preparation Example 2 was used instead ofCompound Inv 3 used in Synthesis Example 88.

HRMS [M]⁺: 656.221

[Synthesis Example 115] Synthesis of Cpd162

Compound Cpd162 (3.9 g, yield 60%) was obtained by performing the sameprocess as in Synthesis Example 89, except that Compound Inv 4 (3.1 g,10.0 mmol) synthesized in Preparation Example 2 was used instead ofCompound Inv 3 used in Synthesis Example 89.

HRMS [M]⁺: 654.230

[Synthesis Example 116] Synthesis of Cpd163

Compound Cpd163 (4.4 g, yield 68%) was obtained by performing the sameprocess as in Synthesis Example 90, except that Compound Inv 4 (3.1 g,10.0 mmol) synthesized in Preparation Example 2 was used instead ofCompound Inv 3 used in Synthesis Example 90.

HRMS [M]⁺: 655.226

[Synthesis Example 117] Synthesis of Cpd164

Compound Cpd164 (4.0 g, yield 60%) was obtained by performing the sameprocess as in Synthesis Example 91, except that Compound Inv 8 (3.1 g,10.0 mmol) synthesized in Preparation Example 4 was used instead ofCompound Inv 7 used in Synthesis Example 91.

HRMS [M]⁺: 656.221

[Synthesis Example 118] Synthesis of Cpd165

Compound Cpd165 (4.0 g, yield 62%) was obtained by performing the sameprocess as in Synthesis Example 92, except that Compound Inv 8 (3.1 g,10.0 mmol) synthesized in Preparation Example 4 was used instead ofCompound Inv 7 used in Synthesis Example 92.

HRMS [M]⁺: 655.226

[Example 1] Manufacture of Green Organic Electroluminescent Device

Compound Cpd1 synthesized in Synthesis Example 1 was subjected to highlypure sublimation purification by a typically known method, and then agreen organic electroluminescent device was manufactured as follows.

A glass substrate thinly coated with indium tin oxide (ITO) having athickness of 1,500 Å was ultrasonically washed with distilled water.When the washing with distilled water was completed, the substrate wasultrasonically washed with a solvent such as isopropyl alcohol, acetone,and methanol, dried, transferred to a UV ozone cleaner (Power sonic 405,manufactured by Hwashin Tech), washed for 5 minutes by using UV, andthen transferred to a vacuum evaporator.

An organic electroluminescent device was manufactured by laminatingm-MTDATA (60 nm)/TCTA (80 nm)/Compound Cpd1 (40 nm)/CBP+10% Ir(ppy)₃(300 nm)/BCP (10 nm)/Alq₃ (30 nm)/LiF (1 nm)/Al (200 nm) in this orderon the thus prepared ITO transparent electrode.

Here, the structures of m-MTDATA, TCTA, Ir(ppy)₃, CBP, and BCP used areas follows.

[Examples 2 to 58] Manufacture of Green Organic ElectroluminescentDevice

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the compounds described in the followingTable 1 were each used instead of Compound Cpd1 used in Example 1.

[Comparative Example 1] Manufacture of Green Organic ElectroluminescentDevice

A green organic electroluminescent device was manufactured in the samemanner as in Example 1, except that Compound Cpd1 used in Example 1 wasnot used.

Evaluation Example 1

For each of the green organic electroluminescent devices manufactured inExamples 1 to 58 and Comparative Example 1, the driving voltage, currentefficiency, and light emitting peak thereof were measured at a currentdensity of 10 mA/cm², and the results are shown in the following Table1.

TABLE 1 Material of Driving Light Current light emitting voltageemitting efficiency auxiliary layer (V) peak (nm) (cd/A) Example 1 Cpd16.80 517 42.0 Example 2 Cpd2 6.85 518 41.9 Example 3 Cpd3 6.71 520 41.5Example 4 Cpd4 6.85 518 41.8 Example 5 Cpd5 6.85 520 41.8 Example 6 Cpd66.80 519 41.5 Example 7 Cpd7 6.90 518 41.8 Example 8 Cpd8 6.85 520 41.5Example 9 Cpd12 6.73 518 41.5 Example 10 Cpd13 6.74 520 41.8 Example 11Cpd14 6.75 518 41.8 Example 12 Cpd15 6.80 517 41.5 Example 13 Cpd16 6.77518 42.0 Example 14 Cpd17 6.72 520 41.9 Example 15 Cpd18 6.80 518 41.5Example 16 Cpd19 6.69 520 41.8 Example 17 Cpd20 6.82 517 41.8 Example 18Cpd21 6.75 518 41.8 Example 19 Cpd22 6.80 520 42.0 Example 20 Cpd23 6.77518 42.0 Example 21 Cpd24 6.85 520 41.5 Example 22 Cpd25 6.80 519 41.8Example 23 Cpd26 6.90 517 41.8 Example 24 Cpd27 6.70 518 41.5 Example 25Cpd28 6.73 520 41.8 Example 26 Cpd29 6.74 518 42.0 Example 27 Cpd33 6.69520 41.8 Example 28 Cpd34 6.80 520 41.5 Example 29 Cpd35 6.71 519 41.8Example 30 Cpd36 6.85 517 41.5 Example 31 Cpd37 6.69 520 41.8 Example 32Cpd38 6.82 517 41.8 Example 33 Cpd39 6.75 518 41.8 Example 34 Cpd40 6.80520 42.0 Example 35 Cpd41 6.80 520 41.8 Example 36 Cpd42 6.90 518 41.8Example 37 Cpd46 6.75 518 41.9 Example 38 Cpd47 6.80 520 42.0 Example 39Cpd48 6.71 518 41.9 Example 40 Cpd49 6.85 520 41.5 Example 41 Cpd51 6.80518 41.8 Example 42 Cpd52 6.90 520 41.5 Example 43 Cpd54 6.80 520 42.0Example 44 Cpd55 6.90 519 41.9 Example 45 Cpd56 6.70 517 41.5 Example 46Cpd57 6.73 518 41.8 Example 47 Cpd60 6.80 520 41.5 Example 48 Cpd70 6.71519 41.5 Example 49 Cpd71 6.85 517 41.8 Example 50 Cpd72 6.70 518 42.0Example 51 Cpd73 6.70 517 42.0 Example 52 Cpd75 6.73 518 41.9 Example 53Cpd76 6.70 517 41.5 Example 54 Cpd77 6.73 518 41.8 Example 55 Cpd78 6.74520 41.5 Example 56 Cpd79 6.75 518 41.8 Example 57 Cpd80 6.85 517 41.5Example 58 Cpd81 6.80 520 42.0 Comparative — 6.93 516 38.2 Example 1

As shown in Table 1, it could be seen that the green organicelectroluminescent devices in Examples 1 to 58 in which the compounds(Cpd1 to Cpd81) represented by Formula 1 according to the presentdisclosure were used as a material of light emitting auxiliary layer hadslightly lower driving voltages than that of the green organicelectroluminescent device in Comparative Example 1 in which only CBP wasused as a material of light emitting layer without a light emittingauxiliary layer, and had better current efficiencies than that of thegreen organic electroluminescent device in Comparative Example 1.

[Example 59] Manufacture of Red Organic Electroluminescent Device

Compound Cpd1 synthesized in Synthesis Example 1 was subjected to highlypure sublimation purification by a typically known method, and then ared organic electroluminescent device was manufactured as follows.

First, a glass substrate thinly coated with indium tin oxide (ITO)having a thickness of 1,500 Å was ultrasonically washed with distilledwater. When the washing with distilled water was completed, thesubstrate was ultrasonically washed with a solvent such as isopropylalcohol, acetone, and methanol, dried, transferred to a UV ozone cleaner(Power sonic 405, manufactured by Hwashin Tech), washed for 5 minutes byusing UV, and then transferred to a vacuum evaporator.

An organic electroluminescent device was manufactured by laminatingm-MTDATA (60 nm)/TCTA (80 nm)/Compound Cpd1 (40 nm)/CBP+10%(piq)₂Ir(acac) (300 nm)/BCP (10 nm)/Alq₃ (30 nm)/LiF (1 nm)/Al (200 nm)in this order on the thus prepared ITO transparent electrode.

Here, the structures of m-MTDATA, TCTA, CBP, and BCP used are the sameas described in Example 1, and (piq)₂Ir(acac) is as follows.

[Examples 60 to 116] Manufacture of Red Organic ElectroluminescentDevice

A red organic electroluminescent device was manufactured in the samemanner as in Example 59, except that the compounds described in thefollowing Table 2 were each used instead of Compound Cpd1 used inExample 59.

[Comparative Example 2] Manufacture of Red Organic ElectroluminescentDevice

A red organic electroluminescent device was manufactured in the samemanner as in Example 59, except that Compound Cpd1 used in Example 59was not used.

Evaluation Example 2

For each of the red organic electroluminescent devices manufactured inExamples 59 to 116 and Comparative Example 2, the driving voltage andcurrent efficiency thereof were measured at a current density of 10mA/cm², and the results are shown in the following Table 2.

TABLE 2 Material of Driving Current light emitting voltage efficiencyauxiliary layer (V) (cd/A) Example 59 Cpd1 5.15 10.8 Example 60 Cpd25.10 11.2 Example 61 Cpd3 5.15 11.0 Example 62 Cpd4 5.20 10.8 Example 63Cpd5 5.15 11.2 Example 64 Cpd6 5.10 11.0 Example 65 Cpd7 5.15 11.3Example 66 Cpd8 5.10 11.0 Example 67 Cpd12 5.15 11.3 Example 68 Cpd135.20 10.8 Example 69 Cpd14 5.13 11.1 Example 70 Cpd15 5.16 11.5 Example71 Cpd16 5.17 11.6 Example 72 Cpd17 5.14 11.0 Example 73 Cpd18 5.15 10.8Example 74 Cpd19 5.10 11.2 Example 75 Cpd20 5.15 11.0 Example 76 Cpd215.20 11.3 Example 77 Cpd22 5.15 11.0 Example 78 Cpd23 5.10 11.3 Example79 Cpd24 5.15 10.8 Example 80 Cpd25 5.10 11.1 Example 81 Cpd26 5.15 11.5Example 82 Cpd27 5.20 10.8 Example 83 Cpd28 5.13 11.2 Example 84 Cpd295.20 11.0 Example 85 Cpd33 5.15 10.8 Example 86 Cpd34 5.10 11.2 Example87 Cpd35 5.15 11.0 Example 88 Cpd36 5.10 11.3 Example 89 Cpd37 5.15 11.0Example 90 Cpd38 5.20 11.3 Example 91 Cpd39 5.13 10.8 Example 92 Cpd405.16 11.1 Example 93 Cpd41 5.17 11.5 Example 94 Cpd42 5.14 11.6 Example95 Cpd46 5.15 11.0 Example 96 Cpd47 5.10 10.8 Example 97 Cpd48 5.15 11.2Example 98 Cpd49 5.20 11.1 Example 99 Cpd51 5.15 11.5 Example 100 Cpd525.10 11.6 Example 101 Cpd54 5.15 11.0 Example 102 Cpd55 5.10 10.8Example 103 Cpd56 5.15 11.2 Example 104 Cpd57 5.20 11.0 Example 105Cpd60 5.13 11.3 Example 106 Cpd70 5.20 11.0 Example 107 Cpd71 5.15 11.3Example 108 Cpd72 5.10 10.8 Example 109 Cpd73 5.15 11.1 Example 110Cpd75 5.10 11.5 Example 111 Cpd76 5.15 10.8 Example 112 Cpd77 5.15 11.2Example 113 Cpd78 5.10 11.0 Example 114 Cpd79 5.15 10.8 Example 115Cpd80 5.15 11.0 Example 116 Cpd81 5.10 10.8 Comparative — 5.25 8.2Example 2

As shown in Table 2, it could be seen that the red organicelectroluminescent devices in Examples 59 to 116 in which the compounds(Cpd1 to Cpd81) represented by Formula 1 according to the presentdisclosure were used as a material of light emitting auxiliary layer hadslightly lower driving voltages than that of the red organicelectroluminescent device in Comparative Example 2 in which only CBP wasused as a material of light emitting layer without a light emittingauxiliary layer, and had better current efficiencies than that of thered organic electroluminescent device in Comparative Example 2.

[Example 117] Manufacture of Blue Organic Electroluminescent Device

Compound Cpd1 synthesized in Synthesis Example 1 was subjected to highlypure sublimation purification by a typically known method, and then ablue organic electroluminescent device was manufactured as follows.

First, a glass substrate thinly coated with indium tin oxide (ITO)having a thickness of 1,500 Å was ultrasonically washed with distilledwater. When the washing with distilled water was completed, thesubstrate was ultrasonically washed with a solvent such as isopropylalcohol, acetone, and methanol, dried, transferred to a UV ozone cleaner(Power sonic 405, manufactured by Hwashin Tech), washed for 5 minutes byusing UV, and then transferred to a vacuum evaporator.

An organic electroluminescent device was manufactured by laminatingDS-205 (Manufactured by Doosan Corporation Electronics) (80 nm)/NPB (15nm)/Compound Cpd1 (15 nm)/ADN+5% DS-405 (Manufactured by DoosanCorporation Electronics) (300 nm)/BCP (10 nm)/Alq₃ (30 nm)/LiF (1 nm)/Al(200 nm) in this order on the thus prepared ITO transparent electrode.

The BCP used is the same as that described in Example 1, and thestructures of NPB and ADN are the same as those described as follows.

[Examples 118 to 174] Manufacture of Blue Organic ElectroluminescentDevice

A blue organic electroluminescent device was manufactured in the samemanner as in Example 117, except that the compounds described in thefollowing Table 3 were each used instead of Compound Cpd1 used inExample 117.

[Comparative Example 3] Manufacture of Blue Organic ElectroluminescentDevice

A blue organic electroluminescent device was manufactured in the samemanner as in Example 117, except that Compound Cpd1 used in Example 117was not used.

Evaluation Example 3

For each of the blue organic electroluminescent devices manufactured inExamples 117 to 174 and Comparative Example 3, the driving voltage andcurrent efficiency thereof were measured at a current density of 10mA/cm², and the results are shown in the following Table 3.

TABLE 3 Material of Driving Current light emitting voltage efficiencyauxiliary layer (V) (cd/A) Example 117 Cpd1 5.50 6.9 Example 118 Cpd25.60 6.6 Example 119 Cpd3 5.55 6.8 Example 120 Cpd4 5.60 6.9 Example 121Cpd5 5.51 6.6 Example 122 Cpd6 5.55 6.8 Example 123 Cpd7 5.51 6.0Example 124 Cpd8 5.55 6.4 Example 125 Cpd12 5.60 6.0 Example 126 Cpd135.65 6.4 Example 127 Cpd14 5.53 6.5 Example 128 Cpd15 5.56 6.8 Example129 Cpd16 5.49 6.1 Example 130 Cpd17 5.50 6.9 Example 131 Cpd18 5.60 6.6Example 132 Cpd19 5.55 6.8 Example 133 Cpd20 5.60 6.9 Example 134 Cpd215.51 6.6 Example 135 Cpd22 5.55 6.8 Example 136 Cpd23 5.51 6.0 Example137 Cpd24 5.55 6.4 Example 138 Cpd25 5.60 6.5 Example 139 Cpd26 5.65 6.8Example 140 Cpd27 5.53 6.1 Example 141 Cpd28 5.56 6.9 Example 142 Cpd295.49 6.6 Example 143 Cpd33 5.50 6.8 Example 144 Cpd34 5.60 6.9 Example145 Cpd35 5.55 6.4 Example 146 Cpd36 5.60 6.5 Example 147 Cpd37 5.51 6.8Example 148 Cpd38 5.55 6.1 Example 149 Cpd39 5.51 6.9 Example 150 Cpd405.55 6.6 Example 151 Cpd41 5.60 6.8 Example 152 Cpd42 5.65 6.9 Example153 Cpd46 5.53 6.6 Example 154 Cpd47 5.56 6.4 Example 155 Cpd48 5.49 6.5Example 156 Cpd49 5.60 6.8 Example 157 Cpd51 5.55 6.1 Example 158 Cpd525.60 6.9 Example 159 Cpd54 5.51 6.6 Example 160 Cpd55 5.55 6.8 Example161 Cpd56 5.51 6.9 Example 162 Cpd57 5.55 6.6 Example 163 Cpd60 5.60 6.8Example 164 Cpd70 5.65 6.0 Example 165 Cpd71 5.53 6.4 Example 166 Cpd725.60 6.5 Example 167 Cpd73 5.55 6.8 Example 168 Cpd75 5.60 6.1 Example169 Cpd76 5.51 6.9 Example 170 Cpd77 5.55 6.6 Example 171 Cpd78 5.51 6.8Example 172 Cpd79 5.55 6.1 Example 173 Cpd80 5.54 6.3 Example 174 Cpd815.58 6.1 Comparative — 5.60 4.8 Example 3

As shown in Table 3, it could be seen that the blue organicelectroluminescent devices in Examples 117 to 174 in which the compounds(Cpd1 to Cpd81) represented by Formula 1 according to the presentdisclosure were used as a material of light emitting auxiliary layer haddriving voltages similar to that of the blue organic electroluminescentdevice in Comparative Example 3 in which ADN was used as a material oflight emitting layer without a light emitting auxiliary layer, but hadbetter current efficiencies than that of the organic electroluminescentdevice in Comparative Example 3.

[Example 175] Manufacture of Green Organic Electroluminescent Device

Compound Cpd86 synthesized in Synthesis Example 59 was subjected tohighly pure sublimation purification by a typically known method, andthen a green organic electroluminescent device was manufacturedaccording to the following procedure.

First, a glass substrate thinly coated with indium tin oxide (ITO)having a thickness of 1,500 Å was ultrasonically washed with distilledwater. When the washing with distilled water was completed, thesubstrate was ultrasonically washed with a solvent such as isopropylalcohol, acetone, and methanol, dried, transferred to a UV ozone cleaner(Power sonic 405, manufactured by Hwashin Tech), washed for 5 minutes byusing UV, and then transferred to a vacuum evaporator.

An organic electroluminescent device was manufactured by laminatingm-MTDATA (60 nm)/TCTA (80 nm)/Compound Cpd86+10% Ir(ppy)₃ (300 nm)/BCP(10 nm)/Alq₃ (30 nm)/LiF (1 nm)/Al (200 nm) in this order on the thusprepared ITO transparent electrode.

[Examples 176 TO 234] Manufacture of Green Organic ElectroluminescentDevice

A green organic electroluminescent device was manufactured in the samemanner as in Example 175, except that the compounds described in thefollowing Table 4 were each used instead of Compound Cpd86 used inExample 217.

[Comparative Example 4] Manufacture of Green Organic ElectroluminescentDevice

A green organic electroluminescent device was manufactured by the sameprocedure as in Example 175, except that CBP was used instead ofCompound Cpd86 used as a material of light emitting host when a lightemitting layer was formed in Example 175.

Evaluation Example 4

For each of the green organic electroluminescent devices manufactured inExamples 175 to 234 and Comparative Example 4, the driving voltage,current efficiency, and light emitting peak thereof were measured at acurrent density of 10 mA/cm², and the results are shown in the followingTable 4.

TABLE 4 Driving voltage EL peak Current efficiency Sample Host (V) (nm)(cd/A) Example 175 Cpd86 6.63 518 40.5 Example 176 Cpd87 6.78 515 42.4Example 177 Cpd88 6.81 518 41.1 Example 178 Cpd89 6.79 517 40.8 Example179 Cpd90 6.81 518 41.1 Example 180 Cpd91 6.79 517 40.8 Example 181Cpd92 6.78 515 42.4 Example 182 Cpd93 6.81 518 41.1 Example 183 Cpd946.79 517 40.8 Example 184 Cpd95 6.81 518 41.1 Example 185 Cpd96 6.79 51740.8 Example 186 Cpd97 6.79 517 40.8 Example 187 Cpd100 6.81 518 41.1Example 188 Cpd101 6.79 517 40.8 Example 189 Cpd105 6.81 518 41.1Example 190 Cpd106 6.78 515 42.4 Example 191 Cpd110 6.79 517 40.8Example 192 Cpd111 6.79 517 40.8 Example 193 Cpd112 6.81 518 41.1Example 194 Cpd113 6.79 517 40.8 Example 195 Cpd114 6.78 515 42.4Example 196 Cpd115 6.81 518 41.1 Example 197 Cpd116 6.79 517 40.8Example 198 Cpd117 6.81 518 41.1 Example 199 Cpd118 6.79 517 40.8Example 200 Cpd119 6.78 515 42.4 Example 201 Cpd120 6.81 518 41.1Example 202 Cpd121 6.79 517 40.8 Example 203 Cpd122 6.81 518 41.1Example 204 Cpd123 6.79 517 40.8 Example 205 Cpd128 6.79 517 40.8Example 206 Cpd129 6.81 518 41.1 Example 207 Cpd130 6.79 517 40.8Example 208 Cpd131 6.79 517 40.8 Example 209 Cpd132 6.81 518 41.1Example 210 Cpd133 6.78 515 42.4 Example 211 Cpd134 6.81 518 41.1Example 212 Cpd135 6.79 517 40.8 Example 213 Cpd136 6.81 518 41.1Example 214 Cpd137 6.79 517 40.8 Example 215 Cpd138 6.79 517 40.8Example 216 Cpd139 6.81 518 41.1 Example 217 Cpd142 6.78 515 42.4Example 218 Cpd143 6.81 518 41.1 Example 219 Cpd147 6.79 517 40.8Example 220 Cpd148 6.81 518 41.1 Example 221 Cpd152 6.81 518 41.1Example 222 Cpd153 6.79 517 40.8 Example 223 Cpd154 6.79 517 40.8Example 224 Cpd155 6.81 518 41.1 Example 225 Cpd156 6.79 517 40.8Example 226 Cpd157 6.81 518 41.1 Example 227 Cpd158 6.78 515 42.4Example 228 Cpd159 6.81 518 41.1 Example 229 Cpd160 6.79 517 40.8Example 230 Cpd161 6.81 518 41.1 Example 231 Cpd162 6.79 517 40.8Example 232 Cpd163 6.79 517 40.8 Example 233 Cpd164 6.81 518 41.1Example 234 Cpd165 6.79 517 40.8 Comparative CBP 6.93 516 38.2 Example 4

As shown in Table 4, it could be seen that the green organicelectroluminescent devices in Examples 175 to 234 in which CompoundsCpd86 to 165 synthesized in Synthesis Examples 59 to 118 were each usedas a material of light emitting layer exhibited better performances interms of current efficiency and driving voltage than the green organicelectroluminescent device in Comparative Example 4 in which CBP in therelated art was used.

[Example 235] Manufacture of Blue Organic Electroluminescent Device

Compound Cpd105 synthesized in Synthesis Example 77 was subjected tohighly pure sublimation purification by a typically known method, andthen a blue organic electroluminescent device was manufactured accordingto the following procedure.

First, a glass substrate thinly coated with indium tin oxide (ITO)having a thickness of 1,500 Å was ultrasonically washed with distilledwater. When the washing with distilled water was completed, thesubstrate was ultrasonically washed with a solvent such as isopropylalcohol, acetone, and methanol, dried, transferred to a UV ozone cleaner(Power sonic 405, manufactured by Hwashin Tech), washed for 5 minutes byusing UV, and then transferred to a vacuum evaporator.

An organic electroluminescent device was manufactured by laminating CuPc(10 nm)/TPAC (30 nm)/Compound Cpd105+7% Flrpic (300 nm)/Alq₃ (30 nm)/LiF(0.2 nm)/Al (150 nm) in this order on the thus prepared ITO transparentelectrode.

Here, the structures of CuPc, TPAC, and Flrpic used are as follows.

[Examples 236 to 257] Manufacture of Blue Organic ElectroluminescentDevice

A blue organic electroluminescent device was manufactured in the samemanner as in Example 235, except that the compounds described in thefollowing Table 5 were each used instead of Compound Cpd105 used inExample 235.

[Comparative Example 5] Manufacture of Blue Organic ElectroluminescentDevice

A blue organic electroluminescent device was manufactured by the sameprocedure as in Example 235, except that CBP was used instead ofCompound Cpd105 used as a material of light emitting host when a lightemitting layer was formed in Example 235.

Evaluation Example 5

For each of the blue organic electroluminescent devices manufactured inExamples 235 to 257 and Comparative Example 5, the driving voltage,current efficiency, and light emitting peak thereof were measured at acurrent density of 10 mA/cm², and the results are shown in the followingTable 5.

TABLE 5 Driving voltage EL peak Current efficiency Sample Host (V) (nm)(cd/A) Example 235 Cpd105 7.30 474 6.34 Example 236 Cpd106 7.24 475 6.55Example 237 Cpd110 7.24 475 6.55 Example 238 Cpd111 7.15 471 6.94Example 239 Cpd112 7.23 472 6.25 Example 240 Cpd113 7.12 472 5.85Example 241 Cpd114 7.00 472 6.34 Example 242 Cpd115 7.29 473 6.90Example 243 Cpd116 7.30 474 6.34 Example 244 Cpd117 7.24 475 6.55Example 245 Cpd147 7.15 471 6.94 Example 246 Cpd148 7.23 472 6.25Example 247 Cpd152 7.30 474 6.34 Example 248 Cpd153 7.24 475 6.55Example 249 Cpd154 7.15 471 6.94 Example 250 Cpd155 7.23 472 6.25Example 251 Cpd156 7.12 472 5.85 Example 252 Cpd157 7.00 472 6.34Example 253 Cpd158 7.29 473 6.90 Example 254 Cpd159 7.30 474 6.34Example 255 Cpd168 7.24 475 6.55 Example 256 Cpd171 7.24 475 6.55Example 257 Cpd174 7.15 471 6.94 Comparative CBP 7.80 474 5.80 Example 5

As shown in Table 5, it could be seen that the blue organicelectroluminescent devices in Examples 235 to 257 in which the compounds(Compounds Cpd105 to Cpd174) according to the present disclosure wereeach used as a material of light emitting layer exhibited betterperformances in terms of current efficiency and driving voltage than theblue organic electroluminescent device in Comparative Example 5 in whichCBP in the related art was used.

[Example 258] Manufacture of Green Organic Electroluminescent Device

A glass substrate thinly coated with indium tin oxide (ITO) having athickness of 1,500 Å was ultrasonically washed with distilled water.When the washing with distilled water was completed, the substrate wasultrasonically washed with a solvent such as isopropyl alcohol, acetone,and methanol, dried, transferred to a UV ozone cleaner (Power sonic 405,manufactured by Hwashin Tech), washed for 5 minutes by using UV, andthen transferred to a vacuum evaporator.

An organic electroluminescent device was manufactured by laminatingm-MTDATA (60 nm)/Compound Cpd1 (80 nm)/DS-H522+5% DS-501 (Manufacturedby Doosan Corporation Electronics) (300 nm)/BCP (10 nm)/Alq₃ (30 nm)/LiF(1 nm)/Al (200 nm) in this order, as a material of hole transport layer,on the ITO transparent electrode prepared as described above.

[Examples 259 to 315] Manufacture of Green Organic ElectroluminescentDevice

A green organic electroluminescent device was manufactured in the samemanner as in Example 258, except that the compounds described in thefollowing Table 6 were each used instead of Compound Cpd1 used inExample 258.

[Comparative Example 6] Manufacture of Organic Electroluminescent Device

An organic electroluminescent device was manufactured in the same manneras in Example 258, except that NPB was used as a material of holetransport layer instead of Compound Cpd1 used when a hole transportlayer was formed in Example 258.

Evaluation Example 6

For each of the green organic electroluminescent devices manufactured inExamples 258 to 315 and Comparative Example 6, the driving voltage andcurrent efficiency thereof were measured at a current density of 10mA/cm², and the results are shown in the following Table 6.

TABLE 6 Hole transport Driving voltage Current efficiency Sample layer(V) (cd/A) Example 258 Cpd1 4.1 22.2 Example 259 Cpd2 4.3 20.1 Example260 Cpd3 4.4 21.3 Example 261 Cpd4 4.0 22.6 Example 262 Cpd5 4.5 19.5Example 263 Cpd6 4.7 20.1 Example 264 Cpd7 4.3 21.6 Example 265 Cpd8 4.520.5 Example 266 Cpd12 4.7 20.6 Example 267 Cpd13 4.4 21.6 Example 268Cpd14 5.0 20.1 Example 269 Cpd15 5.1 18.6 Example 270 Cpd16 4.3 22.0Example 271 Cpd17 4.6 21.2 Example 272 Cpd18 4.5 21.2 Example 273 Cpd194.4 22.3 Example 274 Cpd20 5.1 18.2 Example 275 Cpd21 5.0 18.9 Example276 Cpd22 4.5 21.7 Example 277 Cpd23 4.7 21.2 Example 278 Cpd24 4.8 20.8Example 279 Cpd25 4.5 21.4 Example 280 Cpd26 5.1 18.2 Example 281 Cpd275.1 18.5 Example 282 Cpd28 4.3 22.3 Example 283 Cpd29 4.6 21.4 Example284 Cpd33 4.8 21.6 Example 285 Cpd34 4.2 22.5 Example 286 Cpd35 4.7 20.6Example 287 Cpd36 4.6 20.2 Example 288 Cpd37 4.2 22.1 Example 289 Cpd384.6 21.2 Example 290 Cpd39 4.8 20.0 Example 291 Cpd40 4.2 22.3 Example292 Cpd41 4.8 21.8 Example 293 Cpd42 5.0 19.2 Example 294 Cpd46 4.5 20.3Example 295 Cpd47 5.3 17.2 Example 296 Cpd48 4.9 20.3 Example 297 Cpd494.0 22.6 Example 298 Cpd51 4.5 19.5 Example 299 Cpd52 4.7 20.1 Example300 Cpd54 4.3 21.6 Example 301 Cpd55 4.5 20.5 Example 302 Cpd56 4.7 20.6Example 303 Cpd57 4.4 21.6 Example 304 Cpd60 4.0 22.6 Example 305 Cpd704.5 19.5 Example 306 Cpd71 4.7 20.1 Example 307 Cpd72 4.3 21.6 Example308 Cpd73 4.5 20.5 Example 309 Cpd75 4.7 20.6 Example 310 Cpd76 4.4 21.6Example 311 Cpd77 5.0 20.1 Example 312 Cpd78 4.5 20.3 Example 313 Cpd795.0 20.2 Example 314 Cpd80 4.9 20.3 Example 315 Cpd81 4.0 22.6Comparative NPB 5.2 18.1 Example 6

As shown in Table 6, it could be seen that the organicelectroluminescent devices in Examples 258 to 315 in which the compounds(Cpd1 to Cpd81) represented by Formula 1 according to the presentdisclosure were used as a material of hole transport layer exhibitedbetter performances in terms of current efficiency and driving voltagethan the organic electroluminescent device in Comparative Example 6 inwhich NPB in the related art was used.

[Example 316] Manufacture of Blue Organic Electroluminescent Device

Compound Cpd86 synthesized in Synthesis Example 59 was subjected tohighly pure sublimation purification by a typically known method, andthen a blue organic electroluminescent device was manufactured asfollows.

A glass substrate thinly coated with indium tin oxide (ITO) having athickness of 1,500 Å was ultrasonically washed with distilled water.When the washing with distilled water was completed, the substrate wasultrasonically washed with a solvent such as isopropyl alcohol, acetone,and methanol, dried, transferred to a UV ozone cleaner (Power sonic 405,manufactured by Hwashin Tech), washed for 5 minutes by using UV, andthen transferred to a vacuum evaporator.

An organic electroluminescent device was manufactured by laminatingDS-205 (Manufactured by Doosan Corporation Electronics) (80 nm)/NPB (15nm)/ADN+5% DS-405 (Manufactured by Doosan Corporation Electronics) (30nm)/Compound Cpd86 (5 nm)/Alq₃ (25 nm)/LiF (1 nm)/Al (200 nm) in thisorder on the ITO transparent electrode prepared as described above.

[Example 317 to 355] Manufacture of Blue Organic ElectroluminescentDevice

A blue organic electroluminescent device was manufactured in the samemanner as in Example 316, except that each compound shown in Table 7 wasused instead of Compound Cpd86 used as a material of electron transportauxiliary layer in Example 316.

[Comparative Example 7] Manufacture of Blue Organic ElectroluminescentDevice

A blue organic electroluminescent device was manufactured in the samemanner as in Example 316, except that Alq₃ being a material of electrontransport layer was deposited to have a thickness of 30 nm instead of 25nm without using Compound Cpd86 used as a material of electron transportauxiliary layer in Example 316.

[Comparative Example 8] Manufacture of Blue Organic ElectroluminescentDevice

An organic electroluminescent device was manufactured in the same manneras in Example 316, except that BCP was used instead of Compound Cpd86used as a material of electron transport auxiliary layer in Example 316.

In this case, the structure of BCP used is as follows.

Evaluation Example 7

For each of the organic electroluminescent devices manufactured inExamples 316 to 355 and Comparative Examples 7 and 8, the drivingvoltage, current efficiency, light emitting wavelength, and lifetime(T97) thereof were measured at a current density of 10 mA/cm², and theresults are shown in the following Table 7.

TABLE 7 Light Electron Driving Current emitting transport voltageefficiency peak Lifetime Sample auxiliary layer (V) (cd/A) (nm) (hr,T₉₇) Example 316 Cpd86 4.4 6.2 457 45 Example 317 Cpd87 4.1 6.3 458 62Example 318 Cpd88 4.2 6.6 458 55 Example 319 Cpd89 4.5 6.2 458 75Example 320 Cpd90 4.3 6.5 458 59 Example 321 Cpd91 4.3 6.1 458 78Example 322 Cpd92 4.4 6.4 457 60 Example 323 Cpd93 4.1 6.2 458 64Example 324 Cpd94 4.7 6.0 458 50 Example 325 Cpd95 4.7 6.4 457 85Example 326 Cpd96 4.5 6.1 458 55 Example 327 Cpd97 4.4 6.0 458 75Example 328 Cpd100 4.1 6.3 458 62 Example 329 Cpd101 4.2 6.6 458 55Example 330 Cpd118 4.5 6.2 458 75 Example 331 Cpd119 4.3 6.4 457 60Example 332 Cpd120 4.4 6.2 458 64 Example 333 Cpd121 4.1 6.0 458 50Example 334 Cpd122 4.2 6.4 457 85 Example 335 Cpd123 4.4 6.1 458 55Example 336 Cpd128 4.1 6.0 458 75 Example 337 Cpd129 4.7 6.3 458 62Example 338 Cpd130 4.7 6.4 457 60 Example 339 Cpd131 4.5 6.2 458 64Example 340 Cpd132 4.4 6.0 458 50 Example 341 Cpd133 4.1 6.4 457 85Example 342 Cpd134 4.7 6.1 458 55 Example 343 Cpd135 4.7 6.0 458 75Example 344 Cpd136 4.5 6.3 458 62 Example 345 Cpd137 4.4 6.6 458 55Example 346 Cpd138 4.1 6.2 458 75 Example 347 Cpd139 4.2 6.4 457 60Example 348 Cpd142 4.5 6.2 458 64 Example 349 Cpd143 4.3 6.0 458 50Example 350 Cpd160 4.1 6.4 457 85 Example 351 Cpd161 4.2 6.1 458 55Example 352 Cpd162 4.5 6.0 458 75 Example 353 Cpd163 4.3 6.3 458 62Example 354 Cpd164 4.4 6.6 458 55 Example 355 Cpd165 4.1 6.2 458 75Comparative — 4.7 5.6 458 32 Example 7 Comparative BCP 5.3 5.9 458 28Example 8

As can be seen from Table 7, the blue organic electroluminescent devicesin Examples 316 to 355, in which Compounds Cpd86 to 165 synthesized inSynthesis Examples 59 to 118 were used as a material of electrontransport auxiliary layer, had a driving voltage which is similar to orslightly better than that of the blue organic electroluminescent devicein Comparative Example 7 in which an electron transport auxiliary layerwas not used, but had the significantly improved current efficiency andlifetime.

Further, the blue organic electroluminescent devices in Examples 316 to355 had better driving voltage and current efficiency than those of theblue organic electroluminescent device in Comparative Example 8, inwhich the BCP in the related art was used as a material of electrontransport auxiliary layer, and had the significantly improved lifetime.

Although the preferred exemplary embodiments of the present disclosurehave been described above, the present disclosure is not limitedthereto, and various modifications can be made and carried out withinthe scope of the claims and the detailed description of the invention,and also fall within the scope of the invention.

The invention claimed is:
 1. A compound for an organicelectroluminescence represented by any one selected from the followingFormulae 3 to 5:

in Formulae 3 to 5, X₁ is selected from the group consisting of N(Ar₁),O, S, C(Ar₂)(Ar₃), and Si(Ar₄)(Ar₅), with the proviso that, in Formula3, C(Ar₂)(Ar₃) is excluded from X₁, Y₁ to Y₄ are each independently N orC(R₉), Ar₁ to Ar₅ are the same as or different from each other, and areeach independently selected from the group consisting of a C₁ to C₄₀alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃to C₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclearatoms, a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclearatoms, a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ toC₄₀ alkylsilyl group, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀alkylboron group, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphinegroup, a C₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylaminegroup, or optionally combine with an adjacent group to form a fusedring, R₁ to R₆, R₈, and R₉ are the same as or different from each other,and are each independently selected from the group consisting ofhydrogen, deuterium (D), halogen, a cyano group, a nitro group, a C₁ toC₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, aC₃ to C₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40nuclear atoms, a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60nuclear atoms, a C₁ to C₄₀ alkylsilyl group, a C₆ to C₆₀ arylsilylgroup, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylboron group, a C₆to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxide group, and aC₆ to C₆₀ arylamine group, or R₁ to R₄, and R₉ optionally combine withan adjacent group to form a fused ring, and the alkyl group, the alkenylgroup, the alkynyl group, the cycloalkyl group, the heterocycloalkylgroup, the aryl group, the heteroaryl group, the alkyloxy group, thearyloxy group, the alkylsilyl group, the arylsilyl group, the alkylborongroup, the arylboron group, the arylphosphine group, the arylphosphineoxide group, and the arylamine group of Ar₁ to Ar₅ and R₁ to R₆, R₈, andR₉ are each independently unsubstituted or substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, acyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀ arylgroup, a heteroaryl group having 5 to 60 nuclear atoms, a C₁ to C₄₀alkylsilyl group, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylamine group,and in this case, the substituent optionally combines with an adjacentgroup to form a fused ring, and when the substituent is present inplural numbers, the substituents are the same as or different from eachother, with the proviso that where X₁ in the Formula 3 is N(Ar₁), saidAr₁ is selected from the group consisting of a C₁ to C₄₀ alkyl group, aC₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms,a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀alkylsilyl group, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, oroptionally combines with an adjacent group to form a fused ring, withthe proviso that where X₁ in the Formula 5 is O, the case where all ofR₁ to R₅, R₈ and R₉ are hydrogen is excluded.
 2. The compound of claim1, wherein the Y₁ to Y₄ are all C(R₉), and a plurality of C(R₉)'s is thesame as or different from each other, and R₉ is the same as that definedin claim
 1. 3. The compound of claim 1, wherein at least one of the Ar₁to Ar₅, R₁ to R₆, R₅, and R₉ is represented by the following Formula 6:

in Formula 6, * is the location where the at least one of the Ar₁ toAr₅, R₁ to R₆, R₈, and R₉ is bonded to the structure of Formula 3, 4, or5, L₁ is a single bond or selected from the group consisting of a C₆ toC₁₈ arylene group and a heteroarylene group having 5 to 18 nuclearatoms, or optionally combines with an adjacent substituent to form afused ring, and R_(a) and R_(b) are the same as or different from eachother, and are each independently selected from the group consisting ofa C₁ to C₄₀ alkyl group, a C₆ to C₆₀ aryl group, and a heteroaryl grouphaving 5 to 60 nuclear atoms, or a substitution product represented bythe following Formula 7 or 8, or optionally combine with an adjacentsubstituent to form a fused ring,

in Formulae 7 and 8, * is the location where the R_(a) and R_(b) arebonded to the N atom of Formula 6, X and Y are each a 6-memberedaromatic ring, L₁₁ and L₁₂ are each a single bond, or selected from thegroup consisting of a C₆ to C₁₈ arylene group and a heteroarylene grouphaving 5 to 18 nuclear atoms, Ar₆ is selected from the group consistingof a C₆ to C₁₈ aryl group and a heteroaryl group having 5 to 18 nuclearatoms, a, b, and d are each an integer of 0 to 4, and the case where thea, b, and d are 0 means that hydrogen is not substituted with thesubstituent R_(c), R_(d), or R_(f) and when the a, b, and d are each aninteger of 1 to 3, R_(c), R_(d), or R_(f) are each selected from thegroup consisting of deuterium, halogen, a cyano group, a nitro group, aC₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynylgroup, a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclearatoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₃ toC₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclearatoms, a C₆ to C₆₀ arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁to C₄₀ alkylboron group, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀arylphosphine group, a C₆ to C₆₀ arylphosphine oxide group, and a C₆ toC₆₀ arylsilyl group, c is an integer of 0 to 3, and the case where the cis 0 means that hydrogen is not substituted with the substituent R_(c),and when the c is 1 to 3, R_(c) is selected from the group consisting ofdeuterium, halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C₆ to C₆₀aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group,a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, inthis case, a plurality of R_(c)'s is the same as or different from eachother, a plurality of R_(d)'s is the same as or different from eachother, a plurality of R_(e)'s is the same as or different from eachother, and a plurality of R_(f)'s is the same as or different from eachother, and the arylene group and the heteroarylene group of L₁ and thealkyl group, the aryl group, and the heteroaryl group of R_(a) and R_(b)are each independently unsubstituted or substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, acyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroarylgroup having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ toC₄₀ alkyloxy group, a C₆ to C₆₀ arylamine group, a C₃ to C₄₀ cycloalkylgroup, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₁ toC₄₀ alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group.
 4. Thecompound of claim 1, wherein at least one of the Ar₁ to Ar₅, R₁ to R₆,R₈, and R₉ is represented by the following Formula 9:

in Formula 9, * is the location where the at least one of the Ar₁ toAr₅, R₁ to R₆, R₈, and R₉ is bonded to the structure of Formula 3, 4, or5, L₂ is a single bond or selected from the group consisting of a C₆ toC₁₈ arylene group and a heteroarylene group having 5 to 18 nuclearatoms, Z₁ to Z₅ are the same as or different from each other, and areeach independently N or C(R₁₁), and in this case, at least one of the Z₁to Z₅ is N, and when C(R₁₁) is present in plural numbers, a plurality ofC(R₁₁)'s is the same as or different from each other, R₁₁ is selectedfrom the group consisting of hydrogen, deuterium, halogen, a cyanogroup, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroarylgroup having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ toC₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group, a heterocycloalkylgroup having 3 to 40 nuclear atoms, a C₆ to C₆₀ arylamine group, a C₁ toC₄₀ alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, oroptionally combines with an adjacent group to form a fused ring, and thearylene group and the heteroarylene group of L₂ and the alkyl group, thealkenyl group, the alkynyl group, the aryl group, the heteroaryl group,the aryloxy group, the alkyloxy group, the cycloalkyl group, theheterocycloalkyl group, the arylamine group, the alkylsilyl group, thealkylboron group, the arylboron group, the arylphosphine group, thearylphosphine oxide group, and the arylsilyl group of R₁₁ are eachindependently unsubstituted or substituted with one or more substituentsselected from the group consisting of deuterium, halogen, a cyano group,a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroaryl group having5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxygroup, a C₆ to C₆₀ arylamine group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₁ to C₄₀alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylborongroup, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxidegroup, and a C₆ to C₆₀ arylsilyl group.
 5. The compound of claim 1,wherein at least one of the Ar₁ to Ar₅, R₁ to R₆, R₈, and R₉ is selectedfrom the group consisting of substituents represented by the followingFormulae A-1 to A-15:

in Formulae A-1 to A-15, * is the location where the at least one of theAr₁ to Ar₅, R₁ to R₆, R₈, and R₉ is bonded to the structure of Formula3, 4, or 5, L₂ is a single bond or selected from the group consisting ofa C₆ to C₁₈ arylene group and a heteroarylene group having 5 to 18nuclear atoms, when R₁₁ is present in plural numbers, a plurality ofR₁₁'s is the same as or different from each other, R₁₁ is selected fromthe group consisting of hydrogen, deuterium, halogen, a cyano group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ toC₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroaryl group having 5to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxygroup, a C₃ to C₄₀ cycloalkyl group, a heterocycloalkyl group having 3to 40 nuclear atoms, a C₆ to C₆₀ arylamine group, a C₁ to C₄₀ alkylsilylgroup, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylboron group, a C₆to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxide group, and aC₆ to C₆₀ arylsilyl group, or optionally combines with an adjacent groupto form a fused ring, n is an integer of 0 to 4, and when the n is aninteger of 1 to 4, R₂₁ is selected from the group consisting ofdeuterium, halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C₆ to C₆₀aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group,a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, oroptionally combines with an adjacent group to form a fused ring, and thealkyl group, the alkenyl group, the alkynyl group, the aryl group, theheteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkylgroup, the heterocycloalkyl group, the arylamine group, the alkylsilylgroup, the alkylboron group, the arylboron group, the arylphosphinegroup, the arylphosphine oxide group, and the arylsilyl group of R₁₁ andR₂₁ are each independently unsubstituted or substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, acyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroarylgroup having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ toC₄₀ alkyloxy group, a C₆ to C₆₀ arylamine group, a C₃ to C₄₀ cycloalkylgroup, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₁ toC₄₀ alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group.
 6. Thecompound of claim 1, wherein at least one of the Ar₁ to Ar₅, R₁ to R₆,R₅, and R₉ is represented by the following Formula 10 or 11:

in Formulae 10 and 11, * is the location where the at least one of theAr₁ to Ar₅, R₁ to R₆, R₈, and R₉ is bonded to the structure of Formula3, 4, or 5, L₃ and L₄ are each a single bond, or selected from the groupconsisting of a C₆ to C₁₈ arylene group and a heteroarylene group having5 to 18 nuclear atoms, Z₆ to Z₈ are the same as or different from eachother, and are each independently a single bond, or O, S, or N(R₁₆),provided that a case where Z₆ and Z₇ are all a single bond is excluded,in this case, when N(R₁₆) is present in plural numbers, a plurality ofN(R₁₆)'s is the same as or different from each other, R₁₆ is selectedfrom the group consisting of hydrogen, deuterium, halogen, a cyanogroup, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroarylgroup having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ toC₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group, a heterocycloalkylgroup having 3 to 40 nuclear atoms, a C₆ to C₆₀ arylamine group, a C₁ toC₄₀ alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, oroptionally combines with an adjacent group to form a fused ring, e is aninteger of 0 to 3, and when the e is 1 to 3, R₁₂ is selected from thegroup consisting of deuterium, halogen, a cyano group, a nitro group, aC₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynylgroup, a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclearatoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₃ toC₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclearatoms, a C₆ to C₆₀ arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁to C₄₀ alkylboron group, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀arylphosphine group, a C₆ to C₆₀ arylphosphine oxide group, and a C₆ toC₆₀ arylsilyl group, f, g, and h are an integer of 0 to 4, and when thef, g, and h are each an integer of 1 to 4, R₁₃ to R₁₅ are selected fromthe group consisting of deuterium, halogen, a cyano group, a nitrogroup, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀alkynyl group, a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxy group, aC₃ to C₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40nuclear atoms, a C₆ to C₆₀ arylamine group, a C₁ to C₄₀ alkylsilylgroup, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylboron group, a C₆to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxide group, and aC₆ to C₆₀ arylsilyl group, and in this case, the arylene group and theheteroarylene group of L₃ and the alkyl group, the alkenyl group, thealkynyl group, the aryl group, the heteroaryl group, the aryloxy group,the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group,the arylamine group, the alkylsilyl group, the alkylboron group, thearylboron group, the arylphosphine group, the arylphosphine oxide group,and the arylsilyl group of R₁₂ to R₁₆ are each independentlyunsubstituted or substituted with one or more substituents selected fromthe group consisting of deuterium, halogen, a cyano group, a nitrogroup, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀alkynyl group, a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxy group, aC₆ to C₆₀ arylamine group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₁ to C₄₀alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylborongroup, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxidegroup, and a C₆ to C₆₀ arylsilyl group.
 7. The compound of claim 1,wherein the X₁ is N(Ar₁), and the Ar₁ is represented by the followingFormula 12:

in Formula 12, * is the location where the Ar₁ is bonded to the N atomof N(Ar₁), L₅ is a single bond, or selected from the group consisting ofa C₆ to C₆₀ aryl group, m is an integer of 1 and 2, A is a 6-memberedaromatic ring, x is an integer of 0 to 2, and when the x is an integerof 1 and 2, R₃₁ are selected from the group consisting of deuterium (D),halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ toC₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀ cycloalkylgroup, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ toC₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C₁ toC₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkylsilylgroup, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, oroptionally combines with an adjacent group to form a fused ring, and inthis case, when R₃₁ is present in plural numbers, a plurality of R₃₁'sis the same as or different from each other, Y₅ to Y₈ are eachindependently N or C(R₃₆), and in this case, when C(R₃₆) is present inplural numbers, a plurality of C(R₃₆)'s is the same as or different fromeach other, R₃₂ to R₃₆ are the same as or different from each other, andare each independently selected from the group consisting of hydrogen,deuterium (D), halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms,a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms,a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀alkylsilyl group, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, oroptionally combine with an adjacent group to form a fused ring, and thealkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group,the heterocycloalkyl group, the aryl group, the heteroaryl group, thealkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilylgroup, the alkylboron group, the arylboron group, the arylphosphinegroup, the arylphosphine oxide group, and the arylamine group of R₃₁ toR₃₆ are each independently unsubstituted or substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, acyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀ arylgroup, a heteroaryl group having 5 to 60 nuclear atoms, a C₁ to C₄₀alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkylsilyl group,a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, thesubstituent optionally combines with an adjacent group to form a fusedring, and in this case, when the substituent is present in pluralnumbers, the substituents are the same as or different from each other.8. An organic electroluminescent device comprising: an anode; a cathode;and one or more organic material layers interposed between the anode andthe cathode, wherein at least one of the organic material layerscomprises the compound described in claim
 1. 9. The organicelectroluminescent device of claim 8, wherein the one or more organicmaterial layers comprise a hole transport layer, a light emitting layer,and an electron transport layer, and the organic material layercomprising the compound is a light emitting layer or an electrontransport layer.
 10. The organic electroluminescent device of claim 8,wherein the one or more organic material layers comprise a holetransport layer, a light emitting auxiliary layer, a light emittinglayer, and an electron transport layer, and the organic material layercomprising the compound is a light emitting auxiliary layer.
 11. Theorganic electroluminescent device of claim 8, wherein the one or moreorganic material layers comprise a hole transport layer, a lightemitting layer, an electron transport auxiliary layer, and an electrontransport layer, and the organic material layer comprising the compoundis an electron transport auxiliary layer.
 12. The organicelectroluminescent device of claim 8, wherein the Y₁ to Y₄ are allC(R₉), and a plurality of C(R₉)'s is the same as or different from eachother, and R₉ is the same as that defined in claim
 8. 13. The organicelectroluminescent device of claim 8, wherein at least one of the Ar₁ toAr₅, R₁ to R₆, R₈, and R₉ is represented by the following Formula 6:

in Formula 6, * is the location where the at least one of the Ar₁ toAr₅, R₁ to R₆, R₈, and R₉ is bonded to the structure of Formula 3, 4, or5, L₁ is a single bond or selected from the group consisting of a C₆ toC₁₈ arylene group and a heteroarylene group having 5 to 18 nuclearatoms, or optionally combines with an adjacent substituent to form afused ring, and R_(a) and R_(b) are the same as or different from eachother, and are each independently selected from the group consisting ofa C₁ to C₄₀ alkyl group, a C₆ to C₆₀ aryl group, and a heteroaryl grouphaving 5 to 60 nuclear atoms, or represented by the following Formula 7or 8, or optionally combine with an adjacent substituent to form a fusedring,

in Formulae 7 and 8, * is the location where the Ra an Rb are bonded tothe N atom of Formula 6, X and Y are each a 6-membered aromatic ring,L₁₁ and L₁₂ are each a single bond, or selected from the groupconsisting of a C₆ to C₁₈ arylene group and a heteroarylene group having5 to 18 nuclear atoms, Ar₆ is selected from the group consisting of a C₆to C₁₈ aryl group and a heteroaryl group having 5 to 18 nuclear atoms,a, b, and d are each an integer of 0 to 4, and the case where the a, b,and d are 0 means that hydrogen is not substituted with the substituentR_(c), R_(d), or R_(f) and when the a, b, and d are each an integer of 1to 3, R_(c), R_(d), or R_(f) are each selected from the group consistingof deuterium, halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C₆ to C₆₀aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group,a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, cis an integer of 0 to 3, and the case where the c is 0 means thathydrogen is not substituted with the substituent R_(c), and when the cis 1 to 3, R_(c) is selected from the group consisting of deuterium,halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ toC₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, aheteroaryl group having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxygroup, a C₁ to C₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, inthis case, a plurality of R_(c)'s is the same as or different from eachother, a plurality of R_(d)'s is the same as or different from eachother, a plurality of R_(e)'s is the same as or different from eachother, and a plurality of R_(f)'s is the same as or different from eachother, and the arylene group and the heteroarylene group of L₁ and thealkyl group, the aryl group, and the heteroaryl group of R_(a) and R_(b)are each independently unsubstituted or substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, acyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroarylgroup having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ toC₄₀ alkyloxy group, a C₆ to C₆₀ arylamine group, a C₃ to C₄₀ cycloalkylgroup, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₁ toC₄₀ alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group.
 14. Theorganic electroluminescent device of claim 8, wherein at least one ofthe Ar₁ to Ar₅, R₁ to R₆, R₈, and R₉ is represented by the followingFormula 9:

in Formula 9, * is the location where the at least one of the Ar₁ toAr₅, R₁ to R₆, R₈, and R₉ is bonded to the structure of Formula 3, 4, or5, L₂ is a single bond or selected from the group consisting of a C₆ toC₁₈ arylene group and a heteroarylene group having 5 to 18 nuclearatoms, Z₁ to Z₅ are the same as or different from each other, and areeach independently N or C(R₁₁), and in this case, at least one of the Z₁to Z₅ is N, and when C(R₁₁) is present in plural numbers, a plurality ofC(R₁₁)'s is the same as or different from each other, R₁₁ is selectedfrom the group consisting of hydrogen, deuterium, halogen, a cyanogroup, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroarylgroup having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ toC₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group, a heterocycloalkylgroup having 3 to 40 nuclear atoms, a C₆ to C₆₀ arylamine group, a C₁ toC₄₀ alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, oroptionally combines with an adjacent group to form a fused ring, and thearylene group and the heteroarylene group of L₂ and the alkyl group, thealkenyl group, the alkynyl group, the aryl group, the heteroaryl group,the aryloxy group, the alkyloxy group, the cycloalkyl group, theheterocycloalkyl group, the arylamine group, the alkylsilyl group, thealkylboron group, the arylboron group, the arylphosphine group, thearylphosphine oxide group, and the arylsilyl group of R₁₁ are eachindependently unsubstituted or substituted with one or more substituentsselected from the group consisting of deuterium, halogen, a cyano group,a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroaryl group having5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxygroup, a C₆ to C₆₀ arylamine group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₁ to C₄₀alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylborongroup, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxidegroup, and a C₆ to C₆₀ arylsilyl group.
 15. The organicelectroluminescent device of claim 8, wherein at least one of the Ar₁ toAr₅, R₁ to R₆, R₈, and R₉ is selected from the group consisting ofsubstituents represented by the following Formulae A-1 to A-15:

in Formulae A-1 to A-15, * is the location where the at least one of theAr₁ to Ar₅, R₁ to R₆, R₈, and R₉ is bonded to the structure of Formula3, 4, or 5, L₂ is a single bond or selected from the group consisting ofa C₆ to C₁₈ arylene group and a heteroarylene group having 5 to 18nuclear atoms, when R₁₁ is present in plural numbers, a plurality ofR₁₁'s is the same as or different from each other, R₁₁ is selected fromthe group consisting of hydrogen, deuterium, halogen, a cyano group, anitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ toC₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroaryl group having 5to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxygroup, a C₃ to C₄₀ cycloalkyl group, a heterocycloalkyl group having 3to 40 nuclear atoms, a C₆ to C₆₀ arylamine group, a C₁ to C₄₀ alkylsilylgroup, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylboron group, a C₆to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxide group, and aC₆ to C₆₀ arylsilyl group, or optionally combines with an adjacent groupto form a fused ring, n is an integer of 0 to 4, and when the n is aninteger of 1 to 4, R₂₁ is selected from the group consisting ofdeuterium, halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C₆ to C₆₀aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group,a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, oroptionally combines with an adjacent group to form a fused ring, and thealkyl group, the alkenyl group, the alkynyl group, the aryl group, theheteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkylgroup, the heterocycloalkyl group, the arylamine group, the alkylsilylgroup, the alkylboron group, the arylboron group, the arylphosphinegroup, the arylphosphine oxide group, and the arylsilyl group of R₁₁ andR₂₁ are each independently unsubstituted or substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, acyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroarylgroup having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ toC₄₀ alkyloxy group, a C₆ to C₆₀ arylamine group, a C₃ to C₄₀ cycloalkylgroup, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₁ toC₄₀ alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group.
 16. Theorganic electroluminescent device of claim 8, wherein at least one ofthe Ar₁ to Ar₅, R₁ to R₆, R₈, and R₉ is represented by the followingFormula 10 or 11:

in Formulae 10 and 11, * is the location where the at least one of theAr₁ to Ar₅, R₁ to R₆, R₈, and R₉ is bonded to the structure of Formula3, 4, or 5, L₃ and L₄ are each a single bond, or selected from the groupconsisting of a C₆ to C₁₈ arylene group and a heteroarylene group having5 to 18 nuclear atoms, Z₆ to Z₈ are the same as or different from eachother, and are each independently a single bond, or O, S, or N(R₁₆),provided that a case where Z₆ and Z₇ are all a single bond is excluded,in this case, when N(R₁₆) is present in plural numbers, a plurality ofN(R₁₆)'s is the same as or different from each other, R₁₆ is selectedfrom the group consisting of hydrogen, deuterium, halogen, a cyanogroup, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₆ to C₆₀ aryl group, a heteroarylgroup having 5 to 60 nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ toC₄₀ alkyloxy group, a C₃ to C₄₀ cycloalkyl group, a heterocycloalkylgroup having 3 to 40 nuclear atoms, a C₆ to C₆₀ arylamine group, a C₁ toC₄₀ alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylsilyl group, oroptionally combines with an adjacent group to form a fused ring, e is aninteger of 0 to 3, and when the e is 1 to 3, R₁₂ is selected from thegroup consisting of deuterium, halogen, a cyano group, a nitro group, aC₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynylgroup, a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclearatoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxy group, a C₃ toC₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclearatoms, a C₆ to C₆₀ arylamine group, a C₁ to C₄₀ alkylsilyl group, a C₁to C₄₀ alkylboron group, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀arylphosphine group, a C₆ to C₆₀ arylphosphine oxide group, and a C₆ toC₆₀ arylsilyl group, f, g, and h are an integer of 0 to 4, and when thef, g, and h are each an integer of 1 to 4, R₁₃ to R₁₅ are selected fromthe group consisting of deuterium, halogen, a cyano group, a nitrogroup, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀alkynyl group, a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxy group, aC₃ to C₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40nuclear atoms, a C₆ to C₆₀ arylamine group, a C₁ to C₄₀ alkylsilylgroup, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylboron group, a C₆to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxide group, and aC₆ to C₆₀ arylsilyl group, and in this case, the arylene group and theheteroarylene group of L₃ and the alkyl group, the alkenyl group, thealkynyl group, the aryl group, the heteroaryl group, the aryloxy group,the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group,the arylamine group, the alkylsilyl group, the alkylboron group, thearylboron group, the arylphosphine group, the arylphosphine oxide group,and the arylsilyl group of R₁₂ to R₁₆ are each independentlyunsubstituted or substituted with one or more substituents selected fromthe group consisting of deuterium, halogen, a cyano group, a nitrogroup, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀alkynyl group, a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60nuclear atoms, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkyloxy group, aC₆ to C₆₀ arylamine group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₁ to C₄₀alkylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀ arylborongroup, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀ arylphosphine oxidegroup, and a C₆ to C₆₀ arylsilyl group.
 17. The organicelectroluminescent device of claim 9, wherein the X₁ is N(Ar₁), and theAr₁ is represented by the following Formula 11:

in Formula 12, * is the location where the Ar₁ is bonded to the N atomof N(Ar₁), L₅ is a single bond, or selected from the group consisting ofa C₆ to C₆₀ aryl group, m is an integer of 1 and 2, A is a 6-memberedaromatic ring, x is an integer of 0 to 2, and when the x is an integerof 1 and 2, R₃₁ are selected from the group consisting of deuterium (D),halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ toC₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀ cycloalkylgroup, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ toC₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C₁ toC₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkylsilylgroup, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, oroptionally combines with an adjacent group to form a fused ring, and inthis case, when R₃₁ is present in plural numbers, a plurality of R₃₁'sis the same as or different from each other, Y₅ to Y₈ are eachindependently N or C(R₃₆), and in this case, when C(R₃₆) is present inplural numbers, a plurality of C(R₃₆)'s is the same as or different fromeach other, R₃₂ to R₃₆ are the same as or different from each other, andare each independently selected from the group consisting of hydrogen,deuterium (D), halogen, a cyano group, a nitro group, a C₁ to C₄₀ alkylgroup, a C₂ to C₄₀ alkenyl group, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms,a C₆ to C₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms,a C₁ to C₄₀ alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀alkylsilyl group, a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylborongroup, a C₆ to C₆₀ arylboron group, a C₆ to C₆₀ arylphosphine group, aC₆ to C₆₀ arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, oroptionally combine with an adjacent group to form a fused ring, and thealkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group,the heterocycloalkyl group, the aryl group, the heteroaryl group, thealkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilylgroup, the alkylboron group, the arylboron group, the arylphosphinegroup, the arylphosphine oxide group, and the arylamine group of R₃₁ toR₃₆ are each independently unsubstituted or substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, acyano group, a nitro group, a C₁ to C₄₀ alkyl group, a C₂ to C₄₀ alkenylgroup, a C₂ to C₄₀ alkynyl group, a C₃ to C₄₀ cycloalkyl group, aheterocycloalkyl group having 3 to 40 nuclear atoms, a C₆ to C₆₀ arylgroup, a heteroaryl group having 5 to 60 nuclear atoms, a C₁ to C₄₀alkyloxy group, a C₆ to C₆₀ aryloxy group, a C₁ to C₄₀ alkylsilyl group,a C₆ to C₆₀ arylsilyl group, a C₁ to C₄₀ alkylboron group, a C₆ to C₆₀arylboron group, a C₆ to C₆₀ arylphosphine group, a C₆ to C₆₀arylphosphine oxide group, and a C₆ to C₆₀ arylamine group, thesubstituent optionally combines with an adjacent group to form a fusedring, and in this case, when the substituent is present in pluralnumbers, the substituents are the same as or different from each other.